| Date | Time | Type | Home School | Away School | Site |
| THU 3/21 | 3:45 PM | Scrimmage | Westbrook | Sheehan | Westbrook High School - Westbrook HS / MS Tennis Courts |
| FRI 3/22 | 3:30 PM | Scrimmage | Weston | Staples | Weston High School - WHS Tennis Courts |
| MON 3/25 | 3:30 PM | Scrimmage | Lyman Hall | Foran | Doolittle Park - Doolittle Tennis Courts |
| MON 3/25 | 3:30 PM | Scrimmage | Guilford | Westbrook | Guilford High School - GHS Tennis Courts |
| MON 3/25 | 3:45 PM | Scrimmage | Joel Barlow | Pomperaug | Joel Barlow High School - Tennis Courts |
| MON 3/25 | 3:45 PM | Scrimmage | Ridgefield | Weston | Ridgefield High School - RHS Tennis Courts |
| MON 3/25 | 4:15 PM | Scrimmage | Shepaug Valley | | Shepaug Valley High School - Shepaug Valley Tennis Courts |
| TUE 3/26 | 3:00 PM | Scrimmage | New Milford | Danbury | New Milford High School - Tennis Courts - NMHS |
| TUE 3/26 | 3:30 PM | Scrimmage | Conard | Southington | Conard High School - Tennis Courts |
| TUE 3/26 | 3:30 PM | Scrimmage | Enfield | Suffield | Enfield High School - EHS TENNIS COURTS |
| TUE 3/26 | 3:30 PM | Scrimmage | Guilford | Valley Regional | Guilford High School - Guilford racquet club |
| TUE 3/26 | 3:45 PM | Scrimmage | | North Haven | Hamden Hall Country Day |
| TUE 3/26 | 3:45 PM | Scrimmage | Nonnewaug | Watertown | Nonnewaug High School - Tennis Courts |
| TUE 3/26 | 3:45 PM | Scrimmage | Shelton | Masuk | Shelton High School - Tennis Courts |
| TUE 3/26 | 4:00 PM | Scrimmage | Greenwich | | Greenwich High School - Tennis Courts |
| TUE 3/26 | 4:00 PM | Scrimmage | Trumbull | Seymour | Trumbull High School - Tennis Courts |
| WED 3/27 | 3:45 PM | Scrimmage | Hamden | Seymour | Hamden Middle School - Tennis Courts |
| WED 3/27 | 3:45 PM | Scrimmage | Old Lyme | Rocky Hill | Lyme-Old Lyme High School - Tennis Courts |
| WED 3/27 | 3:45 PM | Scrimmage | Shelton | Trumbull | Shelton High School - Tennis Courts |
| WED 3/27 | 3:45 PM | Scrimmage | South Windsor | Ellington | South Windsor High School - Wapping Tennis Courts |
| WED 3/27 | 3:45 PM | Scrimmage | Westbrook | Daniel Hand, Waterford | Westbrook High School - Westbrook HS / MS Tennis Courts |
| WED 3/27 | 4:00 PM | Scrimmage | Nonnewaug | | Nonnewaug High School - Tennis Courts |
| WED 3/27 | 4:00 PM | Scrimmage | Wilton | Weston | Wilton High School - Tennis Courts |
| THU 3/28 | 4:45 PM | League | | Hall | TBA |
| THU 3/28 | Canceled | League | Daniel Hand | Old Lyme | Polson Middle School, Madison - Polson Tennis Courts/DHHS Campus |
| THU 3/28 | Canceled | League | Southington | Manchester | Southington High School - Tennis Courts |
| THU 3/28 | Canceled | Scrimmage | RHAM | Portland | RHAM High School - Tennis Courts |
| THU 3/28 | Canceled | Scrimmage | Stonington | Rocky Hill | Stonington High School - SHS Tennis Courts |
| THU 3/28 | Canceled | Scrimmage | Mercy | Wolcott | Wesleyan University - Tennis Courts |
| THU 3/28 | Postponed | Scrimmage | Wilton | | Wilton High School - Tennis Courts |
| FRI 3/29 | 10:00 AM | Scrimmage | Pomperaug | Naugatuck | Edgewood Bath and Tennis Club - Edgewood Bath and Tennis Club |
| FRI 3/29 | 10:00 AM | Scrimmage | Rocky Hill | Stonington | Rocky Hill High School - tennis courts |
| FRI 3/29 | 9:30 AM | League | Suffield | Litchfield | Suffield High School - Tennis Courts |
| SAT 3/30 | 1:00 PM | Non-League | New Fairfield | Danbury | New Fairfield High School - Tennis Courts |
| SAT 3/30 | 10:00 AM | Non-League | Foran | Jonathan Law | Foran High School - Richard A. Herman Memorial Tennis Courts |
| SAT 3/30 | 10:00 AM | Non-League | Weston | St. Joseph | Weston High School - WHS Tennis Courts |
| SAT 3/30 | 11:00 AM | League | Branford | Staples | Branford High School - Tennis Courts |
| SAT 3/30 | 11:00 AM | League | Watertown | Kennedy | Crestbrook Park - Crestbrook Park Tennis Courts |
| SAT 3/30 | 11:00 AM | League | Holy Cross | Woodland | Holy Cross - Tennis Courts |
| SAT 3/30 | 11:00 AM | League | Wilby | Naugatuck | Wilby High School - Dave Krill Tennis Courts at WHS |
| SAT 3/30 | 11:00 AM | Non-League | North Branford | Lyman Hall | North Branford High School - NBHS Tennis Courts |
| MON 4/1 | 2:30 PM | League | Hall | Maloney | Hall High School - Tennis Courts |
| MON 4/1 | 3:30 PM | League | Holy Cross | Torrington | Holy Cross - Tennis Courts |
| MON 4/1 | 3:30 PM | League | Woodland | Watertown | Woodland High School - Tennis Courts |
| MON 4/1 | 3:30 PM | Non-League | Wilton | | Wilton Middlebrook School - JV Tennis Courts |
| MON 4/1 | 3:45 PM | League | Amity | West Haven | Amity Regional High School - Tennis Courts |
| MON 4/1 | 3:45 PM | League | Branford | Shelton | Branford High School - Tennis Courts |
| MON 4/1 | 3:45 PM | League | Bristol Eastern | Southington | Bristol Eastern High School - Tennis Court |
| MON 4/1 | 3:45 PM | League | Cheshire | Foran | Cheshire High School - Tennis Courts |
| MON 4/1 | 3:45 PM | League | East Haven | Daniel Hand | East Haven High School - Tennis Court |
| MON 4/1 | 3:45 PM | League | Career Magnet | Lyman Hall | Edgewood Park - Tennis Courts |
| MON 4/1 | 3:45 PM | League | Lauralton Hall | Mercy | Eisenhower Park - Eisenhower Park |
| MON 4/1 | 3:45 PM | League | Guilford | Hamden | Guilford High School - GHS Tennis Courts |
| MON 4/1 | 3:45 PM | League | Kennedy | Wilby | John F. Kennedy High School - Tennis Courts |
| MON 4/1 | 3:45 PM | League | Litchfield | Gilbert | Litchfield High School - LHS Tennis Courts |
| MON 4/1 | 3:45 PM | League | Morgan | Portland | Morgan School - Tennis Courts |
| MON 4/1 | 3:45 PM | League | Nonnewaug | Wamogo | Nonnewaug High School - Tennis Courts |
| MON 4/1 | 3:45 PM | League | North Haven | Jonathan Law | North Haven Athletic Complex - Tennis Courts |
| MON 4/1 | 3:45 PM | League | Northwestern | Housatonic Regional | Northwestern Regional H.S. - Tennis Courts |
| MON 4/1 | 3:45 PM | League | Plainville | Windsor | Plainville High School - PHS Tennis Courts |
| MON 4/1 | 3:45 PM | League | Norwich Free Academy | Windham / Windham Tech | Rec Fields - Armstrong Tennis Courts |
| MON 4/1 | 3:45 PM | League | Rocky Hill | Windsor Locks | Rocky Hill High School - tennis courts |
| MON 4/1 | 3:45 PM | League | Sheehan | Sacred Heart Academy | Sheehan High School - Sheehan HS Tennis Courts |
| MON 4/1 | 3:45 PM | League | Shepaug Valley | Thomaston | Shepaug Valley High School - Shepaug Valley Tennis Courts |
| MON 4/1 | 3:45 PM | League | Westbrook | Haddam-Killingworth | Westbrook High School - Westbrook HS / MS Tennis Courts |
| MON 4/1 | 3:45 PM | League | Wethersfield | Rockville | Wethersfield High School - Tennis Courts |
| MON 4/1 | 3:45 PM | Non-League | Immaculate | New Fairfield | Immaculate High School - Rogers Park, Danbury |
| MON 4/1 | 3:45 PM | Non-League | Weston | Fairfield Warde | Weston High School - WHS Tennis Courts |
| MON 4/1 | 3:45 PM | Scrimmage | RHAM | Ellington | RHAM High School - Tennis Courts |
| MON 4/1 | 4:00 PM | League | Coginchaug | Valley Regional | Coginchaug Regional High School - Tennis Courts @ CRHS |
| MON 4/1 | 4:00 PM | League | Lyman Memorial | Waterford | Lyman Memorial High School - Tennis Courts |
| MON 4/1 | 4:00 PM | League | Old Lyme | East Hampton | Lyme-Old Lyme High School - Tennis Courts |
| MON 4/1 | 4:00 PM | League | Newington | Berlin | Newington High School - Tennis Courts |
| MON 4/1 | 4:00 PM | League | St. Bernard | Woodstock Academy | St. Bernard School - Tennis Courts |
| MON 4/1 | 4:00 PM | League | Suffield | Canton | Suffield High School - Tennis Courts |
| MON 4/1 | 4:00 PM | League | Cromwell | Old Saybrook | Watrous park - Watrous park |
| MON 4/1 | 4:00 PM | Scrimmage | Ridgefield | | Ridgefield High School - RHS Tennis Courts |
| MON 4/1 | 4:30 PM | League | Ansonia | St. Paul Catholic | Nolan Field-Ansonia - Nolan Field- Tennis Courts |
| MON 4/1 | 4:30 PM | Scrimmage | Trumbull | Joel Barlow | Trumbull High School - Tennis Courts |
| MON 4/1 | Canceled | Scrimmage | | Greenwich | Greenwich Academy |
| TUE 4/2 | 2:30 PM | Non-League | St. Joseph | Masuk | St. Joseph High School - Trumbull Racquet Club |
| TUE 4/2 | 3:30 PM | League | Glastonbury | East Catholic | East Hartford Racquet Club - Tennis Courts |
| TUE 4/2 | Postponed | League | Southington | Avon | Southington High School - Tennis Courts |
| TUE 4/2 | Postponed | League | BulkeleyHMTCA/Weaver | Bolton | Weaver High School - Tennis Courts |
| TUE 4/2 | Postponed | Non-League | Newtown | Fairfield Ludlowe | Newtown High School - NHS Tennis Courts |
| THU 4/4 | 4:00 PM | Non-League | Fairfield Ludlowe | Joel Barlow | Fairfield Ludlowe High School - Tennis Courts |
| FRI 4/5 | 3:00 PM | League | Stratford | Notre Dame-Fairfield | Flood Middle School - Flood MS Tennis Courts |
| FRI 4/5 | 3:30 PM | League | Holy Cross | Watertown | Holy Cross - Tennis Courts |
| FRI 4/5 | 3:30 PM | League | Seymour | Naugatuck | Seymour High School - Tennis |
| FRI 4/5 | 3:30 PM | League | Woodland | Ansonia | Woodland High School - Tennis Courts |
| FRI 4/5 | 3:45 PM | League | Amity | Cheshire | Amity Regional High School - Tennis Courts |
| FRI 4/5 | 3:45 PM | League | Bethel | Abbott Tech | Bethel High School - BHS Tennis Courts |
| FRI 4/5 | 3:45 PM | League | Bolton | Rockville | Bolton High School - BHS Tennis Courts |
| FRI 4/5 | 3:45 PM | League | Bunnell | Masuk | Bunnell HS - Bunnell Tennis Courts |
| FRI 4/5 | 3:45 PM | League | Lauralton Hall | Sacred Heart Academy | Eisenhower Park - Eisenhower |
| FRI 4/5 | 3:45 PM | League | Enfield | Northwest Catholic | Enfield High School - EHS TENNIS COURTS |
| FRI 4/5 | 3:45 PM | League | Guilford | Daniel Hand | Guilford High School - GHS Tennis Courts |
| FRI 4/5 | 3:45 PM | League | Ledyard | East Lyme | Ledyard High School - Tennis Courts |
| FRI 4/5 | 3:45 PM | League | New Britain | Platt | New Britain High School - Tennis Courts |
| FRI 4/5 | 3:45 PM | League | North Branford | Coginchaug | North Branford High School - NBHS Tennis Courts |
| FRI 4/5 | 3:45 PM | League | North Haven | Branford | North Haven Athletic Complex - Tennis Courts |
| FRI 4/5 | 3:45 PM | League | Northwestern | Nonnewaug | Northwestern Regional H.S. - Tennis Courts |
| FRI 4/5 | 3:45 PM | League | Plainville | Rocky Hill | Plainville High School - PHS Tennis Courts |
| FRI 4/5 | 3:45 PM | League | RHAM | E.O. Smith | RHAM High School - Tennis Courts |
| FRI 4/5 | 3:45 PM | League | Southington | Maloney | Southington High School - Tennis Courts |
| FRI 4/5 | 3:45 PM | League | Stonington | Norwich Free Academy | Stonington High School - SHS Tennis Courts |
| FRI 4/5 | 3:45 PM | League | Valley Regional | Morgan | Valley Regional High School - Tennis Courts |
| FRI 4/5 | 3:45 PM | League | Wamogo | Litchfield | Wamogo Regional High School - Tennis Courts |
| FRI 4/5 | 3:45 PM | League | Waterford | St. Bernard | Waterford High School - Tennis Courts - WHS |
| FRI 4/5 | 3:45 PM | League | Mercy | Sheehan | Wesleyan University - Tennis Courts |
| FRI 4/5 | 3:45 PM | League | West Haven | Foran | West Haven High School - West Haven Tennis Courts |
| FRI 4/5 | 3:45 PM | League | Wilby | Wolcott | Wilby High School - Dave Krill Tennis Courts at WHS |
| FRI 4/5 | 3:45 PM | Non-League | Wilcox Tech | Lyman Hall | Wilcox Tech - Tennis Courts |
| FRI 4/5 | 4:00 PM | League | East Hampton | Portland | East Hampton High School - Tennis Courts |
| FRI 4/5 | 4:00 PM | League | Ellington | Canton | Ellington High School - Tennis Courts |
| FRI 4/5 | 4:00 PM | League | Lyman Memorial | Fitch | Lyman Memorial High School - Tennis Courts |
| FRI 4/5 | 4:00 PM | League | Old Lyme | Old Saybrook | Lyme-Old Lyme High School - Tennis Courts |
| FRI 4/5 | 4:00 PM | League | Thomaston | East Granby | Thomaston High School - Nystrom Park |
| FRI 4/5 | 4:00 PM | League | Cromwell | Westbrook | Watrous park - Watrous park |
| FRI 4/5 | 4:00 PM | League | Wethersfield | Bloomfield | Wethersfield High School - Tennis Courts |
| FRI 4/5 | 4:00 PM | League | Windsor | BulkeleyHMTCA/Weaver | Windsor High School - WHS Tennis Courts |
| FRI 4/5 | 4:00 PM | Non-League | Fairfield Ludlowe | Weston | Fairfield Ludlowe High School - Tennis Courts |
| FRI 4/5 | 4:15 PM | League | Hamden | East Haven | Hamden Middle School - Tennis Courts |
| FRI 4/5 | 4:30 PM | League | Kennedy | St. Paul Catholic | John F. Kennedy High School - Tennis Courts |
| FRI 4/5 | Canceled | League | New Britain | Rocky Hill | New Britain High School - tennis courts |
| SAT 4/6 | 10:00 AM | League | Hamden | Lauralton Hall | Hamden Middle School - Tennis Courts |
| SAT 4/6 | 10:00 AM | League | Killingly | Woodstock Academy | Killingly High School - Tennis Courts |
| SAT 4/6 | 10:00 AM | League | North Branford | Old Lyme | North Branford High School - NBHS Tennis Courts |
| SAT 4/6 | 10:00 AM | Scrimmage | Plainville | Southington | Plainville High School - PHS Tennis Courts |
| SAT 4/6 | 11:00 AM | Non-League | St. Joseph | Seymour | St. Joseph High School - Tennis Courts |
| SAT 4/6 | 12:00 PM | League | New London | Windham / Windham Tech | New London High School - NLHS Tennis Courts |
| MON 4/8 | 10:00 AM | League | Guilford | Glastonbury | Guilford High School - GHS Tennis Courts |
| MON 4/8 | 10:00 AM | League | Cromwell | Portland | Watrous park - Watrous park |
| MON 4/8 | 10:30 AM | League | Westbrook | North Branford | Westbrook High School - Westbrook HS / MS Tennis Courts |
| MON 4/8 | 11:00 AM | League | Shelton | Cheshire | Shelton High School - Tennis Courts |
| MON 4/8 | 3:30 PM | League | Woodland | Wilby | Woodland High School - Tennis Courts |
| MON 4/8 | 3:45 PM | League | Litchfield | Housatonic Regional | Litchfield High School - LHS Tennis Courts |
| MON 4/8 | 3:45 PM | League | New Milford | Stratford | New Milford High School - Tennis Courts - NMHS |
| MON 4/8 | 3:45 PM | League | Shepaug Valley | Northwestern | Shepaug Valley High School - Shepaug Valley Tennis Courts |
| MON 4/8 | 4:00 PM | League | Darien | Norwalk | Darien High School - DHS Tennis Courts |
| MON 4/8 | 4:00 PM | League | Joel Barlow | Brookfield | Joel Barlow High School - Tennis Courts |
| MON 4/8 | 4:00 PM | League | Suffield | Coventry | Suffield High School - Tennis Courts |
| MON 4/8 | 4:00 PM | League | Gilbert | Nonnewaug | Walker Field - Tennis Courts |
| MON 4/8 | 4:00 PM | League | Wilton | Fairfield Warde | Wilton High School - Tennis Courts |
| MON 4/8 | 4:30 PM | League | Watertown | Torrington | Crestbrook Park - Crestbrook Park Tennis Courts |
| MON 4/8 | 4:30 PM | League | Crosby | Holy Cross | Crosby High School - CHS Tennis. Courts |
| MON 4/8 | 4:30 PM | League | Fairfield Ludlowe | Bridgeport Central | Fairfield Ludlowe High School - Tennis Courts |
| MON 4/8 | 4:30 PM | League | Newtown | Pomperaug | Newtown High School - NHS Tennis Courts |
| MON 4/8 | 4:30 PM | League | Thomaston | Wamogo | Thomaston High School - Nystrom Park |
| MON 4/8 | 4:30 PM | League | Notre Dame-Fairfield | Bethel | Veteran's Park - Bridgeport - Tennis Courts |
| MON 4/8 | 4:45 PM | League | New Fairfield | Weston | New Fairfield High School - Tennis Courts |
| MON 4/8 | 5:00 PM | League | Brien McMahon | Greenwich | Brien McMahon High School - Tennis Courts |
| MON 4/8 | 5:00 PM | League | New Canaan | Danbury | New Canaan HS - NCHS Tennis Courts |
| MON 4/8 | 5:00 PM | League | Ridgefield | Staples | Ridgefield High School - RHS Tennis Courts |
| MON 4/8 | 5:00 PM | League | St. Joseph | Stamford | St. Joseph High School - Tennis Courts |
| MON 4/8 | 5:00 PM | League | Trumbull | Westhill | Trumbull High School - Tennis Courts |
| MON 4/8 | 5:15 PM | League | West Haven | Jonathan Law | West Haven High School - West Haven Tennis Courts |
| TUE 4/9 | 3:30 PM | League | Kennedy | Naugatuck | John F. Kennedy High School - Tennis Courts |
| TUE 4/9 | 3:30 PM | League | Seymour | Ansonia | Seymour High School - Tennis |
| TUE 4/9 | 3:45 PM | League | Bethel | Pomperaug | Bethel High School - BHS Tennis Courts |
| TUE 4/9 | 3:45 PM | League | Bristol Central | East Catholic | Bristol Central High School - Tennis Courts |
| TUE 4/9 | 3:45 PM | League | Career Magnet | Hamden | Edgewood Park - Tennis Courts |
| TUE 4/9 | 3:45 PM | League | Stratford | Masuk | Flood Middle School - Flood MS Tennis Courts |
| TUE 4/9 | 3:45 PM | League | Glastonbury | Rocky Hill | Glastonbury High School - Tennis Courts |
| TUE 4/9 | 3:45 PM | League | Jonathan Law | Shelton | Jonathan Law High School - Tennis Courts |
| TUE 4/9 | 3:45 PM | League | Old Saybrook | Westbrook | Old Saybrook High School - Old Saybrook Tennis Courts |
| TUE 4/9 | 3:45 PM | League | Immaculate | Bunnell | Rogers Park (Danbury, CT) - Tennis Courts |
| TUE 4/9 | 3:45 PM | League | Sheehan | Lyman Hall | Sheehan High School - Sheehan HS Tennis Courts |
| TUE 4/9 | 3:45 PM | League | Shepaug Valley | Housatonic Regional | Shepaug Valley High School - Shepaug Valley Tennis Courts |
| TUE 4/9 | 3:45 PM | League | Wilcox Tech | Abbott Tech | Wilcox Tech - Tennis Courts |
| TUE 4/9 | 3:45 PM | Non-League | Foran | Platt Tech | Foran High School - Richard A. Herman Memorial Tennis Courts |
| TUE 4/9 | 3:45 PM | Non-League | Nonnewaug | Brookfield | Nonnewaug High School - Tennis Courts |
| TUE 4/9 | 4:00 PM | League | Danbury | Trumbull | Danbury High School - DHS Tennis Courts |
| TUE 4/9 | 4:00 PM | League | Fairfield Warde | St. Joseph | Fairfield Warde High School - Blake Courts |
| TUE 4/9 | 4:00 PM | League | Norwalk | Wilton | Grassroots Tennis and Education - Grassroots Tennis Courts |
| TUE 4/9 | 4:00 PM | League | Stamford | Brien McMahon | Stamford High School - SHS Tennis Courts |
| TUE 4/9 | 4:00 PM | League | Staples | New Canaan | Staples High School - Staples Tennis Courts |
| TUE 4/9 | 4:00 PM | League | Westhill | Darien | Westhill High School - Westhill Tennis Courts |
| TUE 4/9 | 4:00 PM | League | Woodland | Torrington | Woodland High School - Tennis Courts |
| TUE 4/9 | 4:15 PM | League | Greenwich | Fairfield Ludlowe | Greenwich High School - Tennis Courts |
| TUE 4/9 | 5:00 PM | League | Bridgeport Central | Ridgefield | Bridgeport Central High School - Central High School Tennis Courts |
| WED 4/10 | 10:00 AM | League | Morgan | Cromwell | Morgan School - Tennis Courts |
| WED 4/10 | 11:00 AM | League | Coginchaug | Old Lyme | Coginchaug Regional High School - Tennis Courts @ CRHS |
| WED 4/10 | 11:00 AM | League | Mercy | Guilford | Wesleyan University - Tennis Courts |
| WED 4/10 | 2:30 PM | League | Lyman Hall | West Haven | Doolittle Park - Doolittle Tennis Courts |
| WED 4/10 | 3:30 PM | League | Crosby | Woodland | Crosby High School - CHS Tennis. Courts |
| WED 4/10 | 3:45 PM | League | Abbott Tech | Platt Tech | Abbott V-T School - Abbott Tech Tennis Complex |
| WED 4/10 | 3:45 PM | League | Bethel | Newtown | Bethel High School - BHS Tennis Courts |
| WED 4/10 | 3:45 PM | League | Brookfield | Bunnell | Brookfield High School - BHS Tennis Courts |
| WED 4/10 | 3:45 PM | League | Watertown | Seymour | Crestbrook Park - Crestbrook Park Tennis Courts |
| WED 4/10 | 3:45 PM | League | Jonathan Law | Amity | Jonathan Law High School - Tennis Courts |
| WED 4/10 | 3:45 PM | League | Ansonia | Torrington | Nolan Field-Ansonia - Nolan Field- Tennis Courts |
| WED 4/10 | 3:45 PM | League | North Haven | Lauralton Hall | North Haven Athletic Complex - Tennis Courts |
| WED 4/10 | 3:45 PM | League | Northwestern | Gilbert | Northwestern Regional H.S. - Tennis Courts |
| WED 4/10 | 3:45 PM | League | Sheehan | Daniel Hand | Sheehan High School - Sheehan HS Tennis Courts |
| WED 4/10 | 3:45 PM | League | Shepaug Valley | Wamogo | Shepaug Valley High School - Shepaug Valley Tennis Courts |
| WED 4/10 | 3:45 PM | League | Notre Dame-Fairfield | New Milford | Veteran's Park - Bridgeport - Tennis Courts |
| WED 4/10 | 3:45 PM | League | Weston | Joel Barlow | Weston High School - WHS Tennis Courts |
| WED 4/10 | 3:45 PM | Non-League | Rockville | E.O. Smith | Rockville High School - RHS Tennis Courts |
| WED 4/10 | 4:00 PM | League | Sacred Heart Academy | East Haven | Albertus Magnus - Tennis Courts |
| WED 4/10 | 4:15 PM | League | New Fairfield | Pomperaug | New Fairfield High School - Tennis Courts |
| WED 4/10 | 4:15 PM | League | Wolcott | St. Paul Catholic | Wolcott High School - WHS Tennis Courts |
| THU 4/11 | 2:30 PM | League | West Haven | Platt Tech | West Haven High School - West Haven Tennis Courts |
| THU 4/11 | 4:00 PM | League | Stamford | Bridgeport Central | Stamford High School - SHS Tennis Courts |
| THU 4/11 | Forfeit | League | Abbott Tech | Norwich Tech | Abbott V-T School - Abbott Tech Tennis Complex |
| THU 4/11 | Postponed | League | Wamogo | Gilbert | Wamogo Regional High School - Tennis Courts |
| FRI 4/12 | 1:00 PM | League | North Haven | Lyman Hall | North Haven Health & Racquet - North Haven Health & Racquet |
| SAT 4/13 | 10:00 AM | League | New Canaan | Norwalk | New Canaan HS - NCHS Tennis Courts |
| SAT 4/13 | 10:00 AM | League | Seymour | Crosby | Seymour High School - Tennis |
| SAT 4/13 | 11:00 AM | League | Jonathan Law | Mercy | Jonathan Law High School - Tennis Courts |
| SAT 4/13 | 11:00 AM | League | Old Lyme | Westbrook | Lyme-Old Lyme High School - Tennis Courts |
| SAT 4/13 | 12:00 PM | League | Foran | Branford | Foran High School - Richard A. Herman Memorial Tennis Courts |
| SAT 4/13 | 12:30 PM | League | Naugatuck | St. Paul Catholic | Naugatuck High School - Tennis Courts |
| MON 4/15 | 10:00 AM | League | Bunnell | Weston | Bunnell HS - Bunnell Tennis Courts |
| MON 4/15 | 10:00 AM | League | Joel Barlow | Pomperaug | Joel Barlow High School - Tennis Courts |
| MON 4/15 | 11:00 AM | League | Darien | Stamford | Darien High School - DHS Tennis Courts |
| MON 4/15 | 11:00 AM | League | New Canaan | Fairfield Ludlowe | New Canaan HS - NCHS Tennis Courts |
| MON 4/15 | 11:00 AM | League | Westhill | Danbury | Westhill High School - Westhill Tennis Courts |
| MON 4/15 | 11:00 AM | League | Wilton | Greenwich | Wilton High School - Tennis Courts |
| MON 4/15 | 12:00 PM | League | Holy Cross | Seymour | Holy Cross - Tennis Courts |
| MON 4/15 | 3:45 PM | League | Bolton | East Granby | Bolton High School - BHS Tennis Courts |
| MON 4/15 | 3:45 PM | League | Branford | Lauralton Hall | Branford High School - Tennis Courts |
| MON 4/15 | 3:45 PM | League | Bristol Central | Windsor Locks | Bristol Central High School - Tennis Courts |
| MON 4/15 | 3:45 PM | League | Cheshire | Guilford | Cheshire High School - Tennis Courts |
| MON 4/15 | 3:45 PM | League | Conard | New Britain | Conard High School - Tennis Courts |
| MON 4/15 | 3:45 PM | League | E.O. Smith | Wethersfield | E.O. Smith High School - Tennis Courts |
| MON 4/15 | 3:45 PM | League | East Haven | West Haven | East Haven High School - Tennis Court |
| MON 4/15 | 3:45 PM | League | East Lyme | Waterford | East Lyme High School - Tennis Courts |
| MON 4/15 | 3:45 PM | League | Foran | Hamden | Foran High School - Richard A. Herman Memorial Tennis Courts |
| MON 4/15 | 3:45 PM | League | Haddam-Killingworth | North Branford | Haddam Killingworth High School (HK) - HKHS Tennis Courts |
| MON 4/15 | 3:45 PM | League | Hall | South Windsor | Hall High School - Tennis Courts |
| MON 4/15 | 3:45 PM | League | Lewis Mills | Windsor | Lewis Mills High School - Tennis Courts |
| MON 4/15 | 3:45 PM | League | Lyman Memorial | St. Bernard | Lyman Memorial High School - Tennis Courts |
| MON 4/15 | 3:45 PM | League | Middletown | Bristol Eastern | Middletown Tennis Courts - Beman Tennis Courts |
| MON 4/15 | 3:45 PM | League | New London | Norwich Free Academy | New London High School - NLHS Tennis Courts |
| MON 4/15 | 3:45 PM | League | New Milford | Bethel | New Milford High School - Tennis Courts - NMHS |
| MON 4/15 | 3:45 PM | League | Daniel Hand | Amity | Polson Middle School, Madison - Polson Tennis Courts/DHHS Campus |
| MON 4/15 | 3:45 PM | League | Rocky Hill | Bloomfield | Rocky Hill High School - tennis courts |
| MON 4/15 | 3:45 PM | League | Valley Regional | Cromwell | Valley Regional High School - Tennis Courts |
| MON 4/15 | 3:45 PM | League | Mercy | Shelton | Wesleyan University - Tennis Courts |
| MON 4/15 | 3:45 PM | League | Westbrook | Coginchaug | Westbrook High School - Westbrook HS / MS Tennis Courts |
| MON 4/15 | 3:45 PM | League | East Catholic | Northwest Catholic | Wickham Park - Wickham Park |
| MON 4/15 | 3:45 PM | League | Masuk | Notre Dame-Fairfield | Wolfe Park - Tennis Courts |
| MON 4/15 | 3:45 PM | Non-League | Maloney | Wilcox Tech | Maloney High School - Tennis Courts |
| MON 4/15 | 4:00 PM | League | Sacred Heart Academy | North Haven | Albertus Magnus - Tennis Courts |
| MON 4/15 | 4:00 PM | League | Fairfield Warde | Bridgeport Central | Fairfield Warde High School - Blake Courts |
| MON 4/15 | 4:00 PM | League | Norwalk | Staples | Grassroots Tennis and Education - Grassroots Tennis Courts |
| MON 4/15 | 4:00 PM | League | Old Lyme | Portland | Lyme-Old Lyme High School - Tennis Courts |
| MON 4/15 | 4:00 PM | League | Old Saybrook | Morgan | Old Saybrook High School - Old Saybrook Tennis Courts |
| MON 4/15 | 4:00 PM | League | St. Joseph | Ridgefield | St. Joseph High School - Tennis Courts |
| MON 4/15 | 4:00 PM | League | Trumbull | Brien McMahon | Trumbull High School - Tennis Courts |
| MON 4/15 | 4:00 PM | Non-League | Newington | Wolcott | Newington High School - Tennis Courts |
| MON 4/15 | 4:30 PM | League | St. Paul Catholic | Watertown | Page Park - Tennis Courts |
| MON 4/15 | Canceled | League | Crosby | Kennedy | Crosby High School - CHS Tennis. Courts |
| TUE 4/16 | 10:00 AM | League | Norwalk | Ridgefield | Grassroots Tennis and Education - Grassroots Tennis Courts |
| TUE 4/16 | 11:00 AM | League | Brookfield | New Fairfield | Brookfield High School - BHS Tennis Courts |
| TUE 4/16 | 11:00 AM | League | Westhill | Fairfield Ludlowe | Westhill High School - Westhill Tennis Courts |
| TUE 4/16 | 3:00 PM | League | Fairfield Warde | New Canaan | Fairfield Warde High School - Blake Courts |
| TUE 4/16 | 3:45 PM | League | Branford | Guilford | Branford High School - Tennis Courts |
| TUE 4/16 | 3:45 PM | League | Bloomfield | Platt | Carmen Arace - Tennis Courts |
| TUE 4/16 | 3:45 PM | League | Lyman Hall | Amity | Doolittle Park - Doolittle Tennis Courts |
| TUE 4/16 | 3:45 PM | League | East Granby | Canton | East Granby High School - EGHS Tennis Courts |
| TUE 4/16 | 3:45 PM | League | Windham / Windham Tech | Montville | Eastern Connecticut State University - Tennis Courts |
| TUE 4/16 | 3:45 PM | League | Lauralton Hall | Career Magnet | Eisenhower Park - Eisenhower |
| TUE 4/16 | 3:45 PM | League | Platt Tech | Prince Tech | Eisenhower Park - Eisenhower Park |
| TUE 4/16 | 3:45 PM | League | Hall | Avon | Hall High School - Tennis Courts |
| TUE 4/16 | 3:45 PM | League | Hamden | Mercy | Hamden Middle School - Tennis Courts |
| TUE 4/16 | 3:45 PM | League | Ledyard | Fitch | Ledyard High School - Tennis Courts |
| TUE 4/16 | 3:45 PM | League | Lewis Mills | Manchester | Lewis Mills High School - Tennis Courts |
| TUE 4/16 | 3:45 PM | League | Maloney | Farmington | Maloney High School - Tennis Courts |
| TUE 4/16 | 3:45 PM | League | Immaculate | Stratford | Rogers Park (Danbury, CT) - Tennis Courts |
| TUE 4/16 | 3:45 PM | League | Sheehan | Jonathan Law | Sheehan High School - Sheehan HS Tennis Courts |
| TUE 4/16 | 3:45 PM | League | Valley Regional | East Hampton | Valley Regional High School - Tennis Courts |
| TUE 4/16 | 3:45 PM | League | West Haven | North Haven | West Haven High School - West Haven Tennis Courts |
| TUE 4/16 | 3:45 PM | League | Wilcox Tech | Norwich Tech | Wilcox Tech - Tennis Courts |
| TUE 4/16 | 3:45 PM | League | Windsor | Enfield | Windsor High School - WHS Tennis Courts |
| TUE 4/16 | 4:00 PM | League | Danbury | Brien McMahon | Danbury High School - DHS Tennis Courts |
| TUE 4/16 | 4:00 PM | League | Darien | St. Joseph | Darien High School - DHS Tennis Courts |
| TUE 4/16 | 4:00 PM | League | Ellington | Granby Memorial | Ellington High School - Tennis Courts |
| TUE 4/16 | 4:00 PM | League | Newington | Northwest Catholic | Newington High School - Tennis Courts |
| TUE 4/16 | 4:00 PM | League | Stonington | Killingly | Stonington High School - SHS Tennis Courts |
| TUE 4/16 | 4:00 PM | League | Wilton | Trumbull | Wilton High School - Allen Meadow |
| TUE 4/16 | 4:30 PM | League | Staples | Stamford | Staples High School - Staples Tennis Courts |
| TUE 4/16 | 5:00 PM | League | Bridgeport Central | Greenwich | Bridgeport Central High School - Central High School Tennis Courts |
| WED 4/17 | 10:00 AM | League | Brien McMahon | Staples | Brien McMahon High School - Tennis Courts |
| WED 4/17 | 10:00 AM | League | Pomperaug | Bunnell | Edgewood Bath and Tennis Club - Edgewood Bath and Tennis Club |
| WED 4/17 | 10:30 AM | League | Stratford | Brookfield | Flood Middle School - Flood MS Tennis Courts |
| WED 4/17 | 11:00 AM | League | Fairfield Ludlowe | Danbury | Fairfield Ludlowe High School - Tennis Courts |
| WED 4/17 | 11:00 AM | League | Windham / Windham Tech | Woodstock Academy | Killingly High School - Killingly High School |
| WED 4/17 | 11:00 AM | League | Naugatuck | Wolcott | Naugatuck High School - Tennis Courts |
| WED 4/17 | 11:00 AM | League | Woodland | Seymour | Woodland High School - Tennis Courts |
| WED 4/17 | 12:00 PM | League | Bethel | New Fairfield | Bethel High School - BHS Tennis Courts |
| WED 4/17 | 3:00 PM | League | Trumbull | Fairfield Warde | Trumbull High School - Tennis Courts |
| WED 4/17 | 3:45 PM | League | Amity | North Haven | Amity Regional High School - Tennis Courts |
| WED 4/17 | 3:45 PM | League | Berlin | E.O. Smith | Berlin High School - Tennis Courts |
| WED 4/17 | 3:45 PM | League | Bolton | Windsor Locks | Bolton High School - BHS Tennis Courts |
| WED 4/17 | 3:45 PM | League | Bristol Eastern | Bloomfield | Bristol Eastern High School - Tennis Court |
| WED 4/17 | 3:45 PM | League | Cheshire | Branford | Cheshire High School - Tennis Courts |
| WED 4/17 | 3:45 PM | League | Conard | Northwest Catholic | Conard High School - Tennis Courts |
| WED 4/17 | 3:45 PM | League | East Lyme | Stonington | East Lyme High School - Tennis Courts |
| WED 4/17 | 3:45 PM | League | Prince Tech | Grasso Tech | Elizabeth Park - Elizabeth Park Courts 1,2,3,4,5,6 |
| WED 4/17 | 3:45 PM | League | Enfield | South Windsor | Enfield High School - EHS TENNIS COURTS |
| WED 4/17 | 3:45 PM | League | Foran | East Haven | Foran High School - Richard A. Herman Memorial Tennis Courts |
| WED 4/17 | 3:45 PM | League | Guilford | Lauralton Hall | Guilford High School - GHS Tennis Courts |
| WED 4/17 | 3:45 PM | League | Hamden | West Haven | Hamden Middle School - Tennis Courts |
| WED 4/17 | 3:45 PM | League | Farmington | Glastonbury | Irving Robbins Middle School - Tennis Courts |
| WED 4/17 | 3:45 PM | League | Jonathan Law | Lyman Hall | Jonathan Law High School - Tennis Courts |
| WED 4/17 | 3:45 PM | League | Killingly | New London | Killingly High School - Tennis Courts |
| WED 4/17 | 3:45 PM | League | Morgan | Old Lyme | Morgan School - Tennis Courts |
| WED 4/17 | 3:45 PM | League | New Britain | Newington | New Britain High School - tennis courts |
| WED 4/17 | 3:45 PM | League | New Milford | Masuk | New Milford High School - Tennis Courts - NMHS |
| WED 4/17 | 3:45 PM | League | Platt | Middletown | Platt High School |
| WED 4/17 | 3:45 PM | League | Daniel Hand | Sacred Heart Academy | Polson Middle School, Madison - Polson Tennis Courts/DHHS Campus |
| WED 4/17 | 3:45 PM | League | Norwich Free Academy | Montville | Rec Fields - Armstrong Tennis Courts |
| WED 4/17 | 3:45 PM | League | Rocky Hill | Wethersfield | Rocky Hill High School - tennis courts |
| WED 4/17 | 3:45 PM | League | Sheehan | Shelton | Sheehan High School - Sheehan HS Tennis Courts |
| WED 4/17 | 3:45 PM | League | Simsbury | RHAM | Simsbury High School - Tennis Courts |
| WED 4/17 | 3:45 PM | League | Avon | East Hartford | Sycamore Park - Sycamore Park |
| WED 4/17 | 3:45 PM | League | Tolland | Lewis Mills | Tolland High School - Tennis Courts |
| WED 4/17 | 3:45 PM | League | Valley Regional | North Branford | Valley Regional High School - Tennis Courts |
| WED 4/17 | 3:45 PM | League | Notre Dame-Fairfield | Immaculate | Veteran's Park - Bridgeport - Tennis Courts |
| WED 4/17 | 3:45 PM | League | Mercy | Career Magnet | Wesleyan University - Tennis Courts |
| WED 4/17 | 3:45 PM | League | East Catholic | Southington | Wickham Park - Wickham Park |
| WED 4/17 | 4:00 PM | League | Coginchaug | Portland | Coginchaug Regional High School - Tennis Courts @ CRHS |
| WED 4/17 | 4:00 PM | League | Ellington | Rockville | Ellington High School - Tennis Courts |
| WED 4/17 | 4:00 PM | League | Haddam-Killingworth | Old Saybrook | Haddam Killingworth High School (HK) - HKHS Tennis Courts |
| WED 4/17 | 4:00 PM | League | Cromwell | East Hampton | Watrous park - Watrous park |
| WED 4/17 | 4:15 PM | League | Maloney | Bristol Central | Maloney High School - Tennis Courts |
| THU 4/18 | 5:00 PM | Scrimmage | Woodstock Academy | | Pomfret School - Field House |
| THU 4/18 | Postponed | League | St. Paul Catholic | Torrington | Page Park - Tennis Courts |
| FRI 4/19 | 11:00 AM | League | Kennedy | Seymour | John F. Kennedy High School - Tennis Courts |
| FRI 4/19 | 12:00 PM | League | Danbury | Wilton | Danbury High School - DHS Tennis Courts |
| FRI 4/19 | 3:00 PM | League | Manchester | Platt | Manchester Tennis Courts - Manchester |
| FRI 4/19 | 3:30 PM | Non-League | Granby Memorial | Windsor Locks | Granby Memorial High School - Tennis Courts |
| FRI 4/19 | 3:45 PM | League | Branford | Mercy | Branford High School - Tennis Courts |
| FRI 4/19 | 3:45 PM | League | Bristol Central | Berlin | Bristol Central High School - Tennis Courts |
| FRI 4/19 | 3:45 PM | League | Bristol Eastern | Tolland | Bristol Eastern High School - Tennis Court |
| FRI 4/19 | 3:45 PM | League | Bloomfield | Lewis Mills | Carmen Arace - Tennis Courts |
| FRI 4/19 | 3:45 PM | League | Lyman Hall | Foran | Doolittle Park - Doolittle Tennis Courts |
| FRI 4/19 | 3:45 PM | League | E.O. Smith | Maloney | E.O. Smith High School - Tennis Courts |
| FRI 4/19 | 3:45 PM | League | Career Magnet | East Haven | Edgewood Park - Tennis Courts |
| FRI 4/19 | 3:45 PM | League | Lauralton Hall | Cheshire | Eisenhower Park - Eisenhower |
| FRI 4/19 | 3:45 PM | League | Fitch | Stonington | Fitch High School - Main Tennis Courts |
| FRI 4/19 | 3:45 PM | League | Hall | Glastonbury | Hall High School - Tennis Courts |
| FRI 4/19 | 3:45 PM | League | Middletown | Plainville | Middletown Tennis Courts - Beman Tennis Courts |
| FRI 4/19 | 3:45 PM | League | Daniel Hand | North Haven | Polson Middle School, Madison - Polson Tennis Courts/DHHS Campus |
| FRI 4/19 | 3:45 PM | League | Shelton | Hamden | Shelton High School - Tennis Courts |
| FRI 4/19 | 3:45 PM | League | South Windsor | Conard | South Windsor High School - Wapping Tennis Courts |
| FRI 4/19 | 3:45 PM | League | Southington | RHAM | Southington High School - Tennis Courts |
| FRI 4/19 | 3:45 PM | League | Avon | Rocky Hill | Sycamore Park - Sycamore Park |
| FRI 4/19 | 3:45 PM | League | West Haven | Sheehan | West Haven High School - West Haven Tennis Courts |
| FRI 4/19 | 3:45 PM | League | Westbrook | Portland | Westbrook High School - Westbrook HS / MS Tennis Courts |
| FRI 4/19 | 3:45 PM | League | Wethersfield | East Hartford | Wethersfield High School - Tennis Courts |
| FRI 4/19 | 3:45 PM | League | East Catholic | Simsbury | Wickham Park - Wickham Park |
| FRI 4/19 | 3:45 PM | League | Masuk | New Fairfield | Wolfe Park - Tennis Courts |
| FRI 4/19 | 3:45 PM | Non-League | Norwich Tech | Montville | Norwich Technical High School - NTHS Outdoor Athletic Complex |
| FRI 4/19 | 3:45 PM | Non-League | Immaculate | Abbott Tech | Rogers Park (Danbury, CT) - Tennis Courts |
| FRI 4/19 | 3:45 PM | Non-League | Waterford | Guilford | Waterford High School - Tennis Courts - WHS |
| FRI 4/19 | 3:45 PM | Non-League | Wilcox Tech | New Britain | Wilcox Tech - Tennis Courts |
| FRI 4/19 | 4:00 PM | League | Coginchaug | Morgan | Coginchaug Regional High School - Tennis Courts @ CRHS |
| FRI 4/19 | 4:00 PM | League | Ellington | East Granby | Ellington High School - Tennis Courts |
| FRI 4/19 | 4:00 PM | League | Old Lyme | Haddam-Killingworth | Lyme-Old Lyme High School - Tennis Courts |
| FRI 4/19 | 4:00 PM | League | Old Saybrook | Valley Regional | Old Saybrook High School - Old Saybrook Tennis Courts |
| FRI 4/19 | 4:15 PM | League | Greenwich | St. Joseph | Greenwich High School - Tennis Courts |
| FRI 4/19 | 4:30 PM | League | Woodland | St. Paul Catholic | Woodland High School - Tennis Courts |
| SAT 4/20 | 10:00 AM | Non-League | New Britain | Southington | New Britain High School - tennis courts |
| MON 4/22 | 3:00 PM | League | Kennedy | Ansonia | John F. Kennedy High School - Tennis Courts |
| MON 4/22 | 3:30 PM | League | Crosby | Watertown | Crosby High School - CHS Tennis. Courts |
| MON 4/22 | 3:30 PM | League | Torrington | Wilby | Durand St Park - Durand St Park |
| MON 4/22 | 3:30 PM | League | Greenwich | Staples | Greenwich High School - Tennis Courts |
| MON 4/22 | 3:30 PM | League | Holy Cross | Naugatuck | Holy Cross - Tennis Courts |
| MON 4/22 | 3:45 PM | League | Berlin | RHAM | Berlin High School - Tennis Courts |
| MON 4/22 | 3:45 PM | League | Brookfield | Notre Dame-Fairfield | Brookfield High School - BHS Tennis Courts |
| MON 4/22 | 3:45 PM | League | Bunnell | Newtown | Bunnell HS - Bunnell Tennis Courts |
| MON 4/22 | 3:45 PM | League | Conard | Newington | Conard High School - Tennis Courts |
| MON 4/22 | 3:45 PM | League | East Granby | BulkeleyHMTCA/Weaver | East Granby High School - EGHS Tennis Courts |
| MON 4/22 | 3:45 PM | League | East Haven | Lyman Hall | East Haven High School - Tennis Court |
| MON 4/22 | 3:45 PM | League | East Lyme | Ledyard | East Lyme High School - Tennis Courts |
| MON 4/22 | 3:45 PM | League | Lauralton Hall | Hamden | Eisenhower Park - Eisenhower |
| MON 4/22 | 3:45 PM | League | Foran | Career Magnet | Foran High School - Richard A. Herman Memorial Tennis Courts |
| MON 4/22 | 3:45 PM | League | Glastonbury | Wethersfield | Glastonbury High School - Tennis Courts |
| MON 4/22 | 3:45 PM | League | Haddam-Killingworth | Coginchaug | Haddam Killingworth High School (HK) - HKHS Tennis Courts |
| MON 4/22 | 3:45 PM | League | Joel Barlow | New Fairfield | Joel Barlow High School - Tennis Courts |
| MON 4/22 | 3:45 PM | League | Montville | St. Bernard | Leary Park - Tennis Courts |
| MON 4/22 | 3:45 PM | League | Litchfield | Northwestern | Litchfield High School - LHS Tennis Courts |
| MON 4/22 | 3:45 PM | League | Maloney | East Catholic | Maloney High School - Tennis Courts |
| MON 4/22 | 3:45 PM | League | Middletown | Bloomfield | Middletown Tennis Courts - Beman Tennis Courts |
| MON 4/22 | 3:45 PM | League | New Britain | Northwest Catholic | New Britain High School - tennis courts |
| MON 4/22 | 3:45 PM | League | New London | Windham / Windham Tech | New London High School - NLHS Tennis Courts |
| MON 4/22 | 3:45 PM | League | Plainville | Lewis Mills | Plainville High School - PHS Tennis Courts |
| MON 4/22 | 3:45 PM | League | Platt | Bristol Eastern | Platt High School |
| MON 4/22 | 3:45 PM | League | Daniel Hand | Cheshire | Polson Middle School, Madison - Polson Tennis Courts/DHHS Campus |
| MON 4/22 | 3:45 PM | League | Portland | Sheehan | Portland High School - Tennis Courts |
| MON 4/22 | 3:45 PM | League | Rocky Hill | Farmington | Rocky Hill High School - tennis courts |
| MON 4/22 | 3:45 PM | League | Immaculate | New Milford | Rogers Park (Danbury, CT) - Tennis Courts |
| MON 4/22 | 3:45 PM | League | Simsbury | E.O. Smith | Simsbury High School - Tennis Courts |
| MON 4/22 | 3:45 PM | League | Southington | Bristol Central | Southington High School - Tennis Courts |
| MON 4/22 | 3:45 PM | League | Thomaston | Nonnewaug | Thomaston High School - Nystrom Park |
| MON 4/22 | 3:45 PM | League | Tolland | Manchester | Tolland High School - Tennis Courts |
| MON 4/22 | 3:45 PM | League | Housatonic Regional | Wamogo | Town Field - Town Tennis Courts |
| MON 4/22 | 3:45 PM | League | Valley Regional | Old Lyme | Valley Regional High School - Tennis Courts |
| MON 4/22 | 3:45 PM | League | Gilbert | Shepaug Valley | Walker Field - Tennis Courts |
| MON 4/22 | 3:45 PM | League | Westbrook | Morgan | Westbrook High School - Westbrook HS / MS Tennis Courts |
| MON 4/22 | 3:45 PM | League | Masuk | Bethel | Wolfe Park - Tennis Courts |
| MON 4/22 | 3:45 PM | Non-League | Platt Tech | Jonathan Law | Eisenhower Park - Eisenhower Park |
| MON 4/22 | 4:00 PM | League | Brien McMahon | Westhill | Brien McMahon High School - Tennis Courts |
| MON 4/22 | 4:00 PM | League | Coventry | Bolton | Coventry High School - tennis courts |
| MON 4/22 | 4:00 PM | League | Fairfield Ludlowe | Norwalk | Fairfield Ludlowe High School - Tennis Courts |
| MON 4/22 | 4:00 PM | League | Canton | Granby Memorial | Mills Pond Park - Canton - Mills Pond |
| MON 4/22 | 4:00 PM | League | New Canaan | Wilton | New Canaan HS - NCHS Tennis Courts |
| MON 4/22 | 4:00 PM | League | Ridgefield | Fairfield Warde | Ridgefield High School - RHS Tennis Courts |
| MON 4/22 | 4:00 PM | League | St. Joseph | Bridgeport Central | St. Joseph High School - Tennis Courts |
| MON 4/22 | 4:00 PM | League | Stamford | Danbury | Stamford High School - SHS Tennis Courts |
| MON 4/22 | 4:00 PM | League | Trumbull | Darien | Trumbull High School - Tennis Courts |
| MON 4/22 | 4:30 PM | League | St. Paul Catholic | Seymour | Page Park - Tennis Courts |
| MON 4/22 | 5:00 PM | League | Woodland | Wolcott | Woodland High School - Tennis Courts |
| TUE 4/23 | 3:15 PM | League | St. Paul Catholic | Holy Cross | Page Park - Tennis Courts |
| TUE 4/23 | 3:30 PM | League | Crosby | Ansonia | Crosby High School - CHS Tennis. Courts |
| TUE 4/23 | 3:30 PM | League | Avon | Maloney | Sycamore Park - Sycamore Park |
| TUE 4/23 | 3:30 PM | Non-League | Abbott Tech | New Fairfield | Abbott V-T School - Abbott Tech Tennis Complex |
| TUE 4/23 | 3:45 PM | League | Berlin | Simsbury | Berlin High School - Tennis Courts |
| TUE 4/23 | 3:45 PM | League | Bunnell | New Milford | Bunnell HS - Bunnell Tennis Courts |
| TUE 4/23 | 3:45 PM | League | Watertown | Wilby | Crestbrook Park - Crestbrook Park Tennis Courts |
| TUE 4/23 | 3:45 PM | League | E.O. Smith | East Hartford | E.O. Smith High School - Tennis Courts |
| TUE 4/23 | 3:45 PM | League | East Haven | Sacred Heart Academy | East Haven High School - Tennis Court |
| TUE 4/23 | 3:45 PM | League | East Lyme | Montville | East Lyme High School - Tennis Courts |
| TUE 4/23 | 3:45 PM | League | Career Magnet | Guilford | Edgewood Park - Tennis Courts |
| TUE 4/23 | 3:45 PM | League | Prince Tech | Norwich Tech | Elizabeth Park - Elizabeth Park Courts 1,2,3,4,5,6 |
| TUE 4/23 | 3:45 PM | League | Enfield | Rocky Hill | Enfield High School - EHS TENNIS COURTS |
| TUE 4/23 | 3:45 PM | League | Haddam-Killingworth | Cromwell | Haddam Killingworth High School (HK) - HKHS Tennis Courts |
| TUE 4/23 | 3:45 PM | League | Killingly | Ledyard | Killingly High School - Tennis Courts |
| TUE 4/23 | 3:45 PM | League | Litchfield | Shepaug Valley | Litchfield High School - LHS Tennis Courts |
| TUE 4/23 | 3:45 PM | League | Manchester | Plainville | Manchester Tennis Courts - Manchester |
| TUE 4/23 | 3:45 PM | League | Rockville | Windsor Locks | Rockville High School - RHS Tennis Courts |
| TUE 4/23 | 3:45 PM | League | Immaculate | Newtown | Rogers Park (Danbury, CT) - Tennis Courts |
| TUE 4/23 | 3:45 PM | League | Shelton | West Haven | Shelton High School - Tennis Courts |
| TUE 4/23 | 3:45 PM | League | Windsor | South Windsor | Windsor High School - WHS Tennis Courts |
| TUE 4/23 | 3:45 PM | League | Masuk | Joel Barlow | Wolfe Park - Tennis Courts |
| TUE 4/23 | 3:45 PM | Non-League | Wilcox Tech | North Haven | Wilcox Tech - Tennis Courts |
| TUE 4/23 | 4:00 PM | League | Darien | Bridgeport Central | Darien High School - DHS Tennis Courts |
| TUE 4/23 | 4:00 PM | League | Fairfield Ludlowe | St. Joseph | Fairfield Ludlowe High School - Tennis Courts |
| TUE 4/23 | 4:00 PM | League | Fairfield Warde | Danbury | Fairfield Warde High School - Blake Courts |
| TUE 4/23 | 4:00 PM | League | Norwalk | Westhill | Grassroots Tennis and Education - Grassroots Tennis Courts |
| TUE 4/23 | 4:00 PM | League | New Canaan | Stamford | New Canaan HS - NCHS Tennis Courts |
| TUE 4/23 | 4:00 PM | League | Newington | Middletown | Newington High School - Tennis Courts |
| TUE 4/23 | 4:00 PM | League | Ridgefield | Brien McMahon | Ridgefield High School - RHS Tennis Courts |
| TUE 4/23 | 4:00 PM | League | Suffield | Ellington | Suffield High School - Tennis Courts |
| TUE 4/23 | 4:00 PM | League | Trumbull | Greenwich | Trumbull High School - Tennis Courts |
| TUE 4/23 | 4:00 PM | League | Wilton | Staples | Wilton High School - Tennis Courts |
| TUE 4/23 | 4:45 PM | League | Weston | Stratford | Weston High School - WHS Tennis Courts |
| TUE 4/23 | Postponed | League | Coginchaug | East Hampton | Coginchaug Regional High School - Tennis Courts @ CRHS |
| WED 4/24 | 3:00 PM | League | Wilby | Ansonia | Wilby High School - Dave Krill Tennis Courts at WHS |
| WED 4/24 | 3:30 PM | League | Newtown | Brookfield | Treadwell Park - Newtown Treadwell Park |
| WED 4/24 | 3:30 PM | League | Wilby | Ansonia | Wilby High School - Dave Krill Tennis Courts at WHS |
| WED 4/24 | 3:30 PM | League | Wolcott | Woodland | Wolcott High School - WHS Tennis Courts |
| WED 4/24 | 3:45 PM | League | Bristol Central | Wethersfield | Bristol Central High School - Tennis Courts |
| WED 4/24 | 3:45 PM | League | Conard | Platt | Conard High School - Tennis Courts |
| WED 4/24 | 3:45 PM | League | East Granby | Rockville | East Granby High School - EGHS Tennis Courts |
| WED 4/24 | 3:45 PM | League | East Hartford | East Catholic | East Hartford High School - Tennis Courts |
| WED 4/24 | 3:45 PM | League | Pomperaug | Weston | Edgewood Bath and Tennis Club - Edgewood Bath and Tennis Club |
| WED 4/24 | 3:45 PM | League | Enfield | Tolland | Enfield High School - EHS TENNIS COURTS |
| WED 4/24 | 3:45 PM | League | Stratford | Bethel | Flood Middle School - Flood MS Tennis Courts |
| WED 4/24 | 3:45 PM | League | Glastonbury | E.O. Smith | Glastonbury High School - Tennis Courts |
| WED 4/24 | 3:45 PM | League | Hall | RHAM | Hall High School - Tennis Courts |
| WED 4/24 | 3:45 PM | League | Hamden | Guilford | Hamden Middle School - Tennis Courts |
| WED 4/24 | 3:45 PM | League | Farmington | Southington | Irving Robbins Middle School - Tennis Courts |
| WED 4/24 | 3:45 PM | League | Jonathan Law | North Haven | Jonathan Law High School - Tennis Courts |
| WED 4/24 | 3:45 PM | League | Litchfield | Thomaston | Litchfield High School - LHS Tennis Courts |
| WED 4/24 | 3:45 PM | League | New Britain | Bristol Eastern | New Britain High School - tennis courts |
| WED 4/24 | 3:45 PM | League | New Fairfield | Immaculate | New Fairfield High School - Tennis Courts |
| WED 4/24 | 3:45 PM | League | Northwestern | Wamogo | Northwestern Regional H.S. - Tennis Courts |
| WED 4/24 | 3:45 PM | League | Daniel Hand | East Haven | Polson Middle School, Madison - Polson Tennis Courts/DHHS Campus |
| WED 4/24 | 3:45 PM | League | Portland | Haddam-Killingworth | Portland High School - Tennis Courts |
| WED 4/24 | 3:45 PM | League | Norwich Free Academy | Killingly | Rec Fields - Armstrong Tennis Courts |
| WED 4/24 | 3:45 PM | League | Rocky Hill | Berlin | Rocky Hill High School - tennis courts |
| WED 4/24 | 3:45 PM | League | Seymour | Torrington | Seymour High School - Tennis |
| WED 4/24 | 3:45 PM | League | Shelton | Branford | Shelton High School - Tennis Courts |
| WED 4/24 | 3:45 PM | League | Shepaug Valley | Nonnewaug | Shepaug Valley High School - Shepaug Valley Tennis Courts |
| WED 4/24 | 3:45 PM | League | South Windsor | Plainville | South Windsor High School - Wapping Tennis Courts |
| WED 4/24 | 3:45 PM | League | Housatonic Regional | Gilbert | Town Field - Town Tennis Courts |
| WED 4/24 | 3:45 PM | League | Valley Regional | Westbrook | Valley Regional High School - Tennis Courts |
| WED 4/24 | 3:45 PM | League | Waterford | Windham / Windham Tech | Waterford High School - Tennis Courts - WHS |
| WED 4/24 | 3:45 PM | League | Mercy | Lauralton Hall | Wesleyan University - Tennis Courts |
| WED 4/24 | 3:45 PM | League | West Haven | Amity | West Haven High School - West Haven Tennis Courts |
| WED 4/24 | 3:45 PM | League | Windsor | Bloomfield | Windsor High School - WHS Tennis Courts |
| WED 4/24 | 3:45 PM | Non-League | Platt Tech | Sheehan | Eisenhower Park - Eisenhower Park |
| WED 4/24 | 3:45 PM | Non-League | Granby Memorial | Lewis Mills | Granby Memorial High School - Tennis Courts |
| WED 4/24 | 4:00 PM | League | Brien McMahon | Fairfield Ludlowe | Brien McMahon High School - Tennis Courts |
| WED 4/24 | 4:00 PM | League | Ellington | Bolton | Ellington High School - Tennis Courts |
| WED 4/24 | 4:00 PM | League | Ledyard | Woodstock Academy | Ledyard High School - Tennis Courts |
| WED 4/24 | 4:00 PM | League | Newington | Manchester | Newington High School - Tennis Courts |
| WED 4/24 | 4:00 PM | League | Stonington | Lyman Memorial | Stonington High School - SHS Tennis Courts |
| WED 4/24 | 4:00 PM | League | Suffield | Windsor Locks | Suffield High School - Tennis Courts |
| WED 4/24 | 4:00 PM | League | Cromwell | Old Lyme | Watrous park - Watrous park |
| WED 4/24 | 4:30 PM | League | Naugatuck | Watertown | Naugatuck High School - Tennis Courts |
| WED 4/24 | 4:30 PM | League | Stamford | Ridgefield | Stamford High School - SHS Tennis Courts |
| WED 4/24 | 5:00 PM | League | Bridgeport Central | Trumbull | Bridgeport Central High School - Central High School Tennis Courts |
| WED 4/24 | 5:00 PM | League | Darien | Wilton | Darien High School - DHS Tennis Courts |
| THU 4/25 | 3:00 PM | League | E.O. Smith | East Catholic | E.O. Smith High School - Tennis Courts |
| THU 4/25 | 3:00 PM | League | Nonnewaug | Litchfield | Nonnewaug High School - Tennis Courts |
| THU 4/25 | 3:30 PM | League | East Hartford | Hall | East Hartford High School - Tennis Courts |
| THU 4/25 | 3:30 PM | League | Kennedy | Crosby | John F. Kennedy High School - Tennis Courts |
| THU 4/25 | 3:30 PM | League | Wolcott | Seymour | Wolcott High School - WHS Tennis Courts |
| THU 4/25 | 3:45 PM | League | Branford | Foran | Branford High School - Tennis Courts |
| THU 4/25 | 3:45 PM | League | Lyman Hall | Career Magnet | Doolittle Park - Doolittle Tennis Courts |
| THU 4/25 | 3:45 PM | League | East Granby | Windsor Locks | East Granby High School - EGHS Tennis Courts |
| THU 4/25 | 3:45 PM | League | East Lyme | Fitch | East Lyme High School - Tennis Courts |
| THU 4/25 | 3:45 PM | League | Morgan | East Hampton | Morgan School - Tennis Courts |
| THU 4/25 | 3:45 PM | League | North Haven | West Haven | North Haven Athletic Complex - Tennis Courts |
| THU 4/25 | 3:45 PM | League | Norwich Tech | Grasso Tech | Norwich Technical High School - NTHS Outdoor Athletic Complex |
| THU 4/25 | 3:45 PM | League | Rocky Hill | Bristol Eastern | Rocky Hill High School - tennis courts |
| THU 4/25 | 3:45 PM | League | Thomaston | Shepaug Valley | Thomaston High School - Nystrom Park |
| THU 4/25 | 3:45 PM | League | Valley Regional | Portland | Valley Regional High School - Tennis Courts |
| THU 4/25 | 3:45 PM | League | Mercy | Jonathan Law | Wesleyan University - Tennis Courts |
| THU 4/25 | 3:45 PM | Non-League | Lauralton Hall | Platt Tech | Eisenhower Park - Eisenhower Park |
| THU 4/25 | 3:45 PM | Non-League | BulkeleyHMTCA/Weaver | Prince Tech | Weaver High School - Tennis Courts |
| THU 4/25 | 4:00 PM | League | Sacred Heart Academy | Sheehan | Albertus Magnus - Tennis Courts |
| THU 4/25 | 4:00 PM | League | Coginchaug | Cromwell | Coginchaug Regional High School - Tennis Courts @ CRHS |
| THU 4/25 | 4:00 PM | League | Danbury | Greenwich | Danbury High School - DHS Tennis Courts |
| THU 4/25 | 4:00 PM | League | Darien | New Canaan | Darien High School - DHS Tennis Courts |
| THU 4/25 | 4:00 PM | League | Fairfield Warde | Fairfield Ludlowe | Fairfield Warde High School - Blake Courts |
| THU 4/25 | 4:00 PM | League | Norwalk | Brien McMahon | Grassroots Tennis and Education - Grassroots Tennis Courts |
| THU 4/25 | 4:00 PM | League | St. Joseph | Trumbull | St. Joseph High School - Tennis Courts |
| THU 4/25 | 4:00 PM | League | Staples | Bridgeport Central | Staples High School - Staples Tennis Courts |
| THU 4/25 | 4:00 PM | League | Westhill | Stamford | Westhill High School - Westhill Tennis Courts |
| THU 4/25 | 4:00 PM | League | Wilton | Ridgefield | Wilton High School - Tennis Courts |
| THU 4/25 | 4:00 PM | Non-League | Old Saybrook | New London | Old Saybrook High School - Old Saybrook Tennis Courts |
| THU 4/25 | 4:30 PM | League | Kennedy | Crosby | John F. Kennedy High School - Tennis Courts |
| THU 4/25 | 4:30 PM | League | South Windsor | Newington | South Windsor High School - Wapping Tennis Courts |
| FRI 4/26 | 3:30 PM | League | Holy Cross | Ansonia | Holy Cross - Holy Cross |
| FRI 4/26 | 3:30 PM | League | Old Lyme | Coginchaug | Lyme-Old Lyme High School - Tennis Courts |
| FRI 4/26 | 3:30 PM | League | Naugatuck | Torrington | Naugatuck High School - Tennis Courts |
| FRI 4/26 | 3:30 PM | League | Westhill | Fairfield Warde | Westhill High School - Westhill Tennis Courts |
| FRI 4/26 | 3:45 PM | League | Amity | Lyman Hall | Amity Regional High School - Tennis Courts |
| FRI 4/26 | 3:45 PM | League | Bristol Eastern | Manchester | Bristol Eastern High School - Tennis Court |
| FRI 4/26 | 3:45 PM | League | Conard | Windsor | Conard High School - Tennis Courts |
| FRI 4/26 | 3:45 PM | League | Coventry | Ellington | Coventry High School - tennis courts |
| FRI 4/26 | 3:45 PM | League | East Hartford | Glastonbury | East Hartford High School - Tennis Courts |
| FRI 4/26 | 3:45 PM | League | Enfield | New Britain | Enfield High School - EHS TENNIS COURTS |
| FRI 4/26 | 3:45 PM | League | Guilford | Career Magnet | Guilford High School - GHS Tennis Courts |
| FRI 4/26 | 3:45 PM | League | Farmington | Avon | Irving Robbins Middle School - Tennis Courts |
| FRI 4/26 | 3:45 PM | League | Joel Barlow | Immaculate | Joel Barlow High School - Tennis Courts |
| FRI 4/26 | 3:45 PM | League | Ledyard | Norwich Free Academy | Ledyard High School - Tennis Courts |
| FRI 4/26 | 3:45 PM | League | Lewis Mills | Middletown | Lewis Mills High School - Tennis Courts |
| FRI 4/26 | 3:45 PM | League | Maloney | Simsbury | Maloney High School - Tennis Courts |
| FRI 4/26 | 3:45 PM | League | New London | Montville | New London High School - NLHS Tennis Courts |
| FRI 4/26 | 3:45 PM | League | Plainville | Bloomfield | Plainville High School - PHS Tennis Courts |
| FRI 4/26 | 3:45 PM | League | RHAM | Bristol Central | RHAM High School - Tennis Courts |
| FRI 4/26 | 3:45 PM | League | Rockville | Granby Memorial | Rockville High School - RHS Tennis Courts |
| FRI 4/26 | 3:45 PM | League | Shelton | Sheehan | Shelton High School - Tennis Courts |
| FRI 4/26 | 3:45 PM | League | Southington | Berlin | Southington High School - Tennis Courts |
| FRI 4/26 | 3:45 PM | League | St. Bernard | Windham / Windham Tech | St. Bernard School - Tennis Courts |
| FRI 4/26 | 3:45 PM | League | Suffield | East Granby | Suffield High School - Tennis Courts |
| FRI 4/26 | 3:45 PM | League | Tolland | Platt | Tolland High School - Tennis Courts |
| FRI 4/26 | 3:45 PM | League | Housatonic Regional | Northwestern | Town Field - Town Tennis Courts |
| FRI 4/26 | 3:45 PM | League | Gilbert | Litchfield | Walker Field - Tennis Courts |
| FRI 4/26 | 3:45 PM | League | Wamogo | Nonnewaug | Wamogo Regional High School - Tennis Courts |
| FRI 4/26 | 3:45 PM | League | Waterford | Stonington | Waterford High School - Tennis Courts - WHS |
| FRI 4/26 | 3:45 PM | League | Weston | Newtown | Weston High School - WHS Tennis Courts |
| FRI 4/26 | 3:45 PM | League | Wethersfield | Hall | Wethersfield High School - Tennis Courts |
| FRI 4/26 | 3:45 PM | League | Wilcox Tech | Platt Tech | Wilcox Tech - Tennis Courts |
| FRI 4/26 | 3:45 PM | Non-League | New Fairfield | Abbott Tech | New Fairfield High School - Tennis Courts |
| FRI 4/26 | 4:00 PM | League | Greenwich | New Canaan | Greenwich High School - Tennis Courts |
| FRI 4/26 | 4:00 PM | League | St. Joseph | Norwalk | St. Joseph High School - Tennis Courts |
| SAT 4/27 | 10:00 AM | League | Tolland | South Windsor | Tolland High School - Tennis Courts |
| SAT 4/27 | 10:00 AM | Non-League | North Branford | Wilcox Tech | North Branford High School - NBHS Tennis Courts |
| SAT 4/27 | 11:00 AM | League | Watertown | Wolcott | Crestbrook Park - Crestbrook Park Tennis Courts |
| SAT 4/27 | 11:00 AM | League | East Lyme | Windham / Windham Tech | East Lyme High School - Tennis Courts |
| SAT 4/27 | 11:00 AM | League | Shelton | Foran | Shelton High School - Tennis Courts |
| SAT 4/27 | 11:00 AM | League | Windsor Locks | Ellington | Windsor Locks High School - Tennis Court |
| SAT 4/27 | 12:00 PM | League | Fitch | Woodstock Academy | Fitch High School - Main Tennis Courts |
| SAT 4/27 | 12:00 PM | Non-League | Mercy | St. Paul Catholic | Wesleyan University - Tennis Courts |
| MON 4/29 | 3:30 PM | League | Crosby | Seymour | Crosby High School - CHS Tennis. Courts |
| MON 4/29 | 3:30 PM | League | Naugatuck | Holy Cross | Naugatuck High School - Tennis Courts |
| MON 4/29 | 3:30 PM | League | Wilby | Kennedy | Wilby High School - Dave Krill Tennis Courts at WHS |
| MON 4/29 | 3:45 PM | League | Bethel | Joel Barlow | Bethel High School - BHS Tennis Courts |
| MON 4/29 | 3:45 PM | League | Branford | North Haven | Branford High School - Tennis Courts |
| MON 4/29 | 3:45 PM | League | Bristol Central | Lewis Mills | Bristol Central High School - Tennis Courts |
| MON 4/29 | 3:45 PM | League | Bristol Eastern | Middletown | Bristol Eastern High School - Tennis Court |
| MON 4/29 | 3:45 PM | League | Cheshire | Amity | Cheshire High School - Tennis Courts |
| MON 4/29 | 3:45 PM | League | Watertown | Woodland | Crestbrook Park - Crestbrook Park Tennis Courts |
| MON 4/29 | 3:45 PM | League | E.O. Smith | RHAM | E.O. Smith High School - Tennis Courts |
| MON 4/29 | 3:45 PM | League | East Hartford | East Catholic | East Hartford High School - Tennis Courts |
| MON 4/29 | 3:45 PM | League | East Haven | Hamden | East Haven High School - Tennis Court |
| MON 4/29 | 3:45 PM | League | Foran | West Haven | Foran High School - Richard A. Herman Memorial Tennis Courts |
| MON 4/29 | 3:45 PM | League | Glastonbury | Farmington | Glastonbury High School - Tennis Courts |
| MON 4/29 | 3:45 PM | League | Granby Memorial | Suffield | Granby Memorial High School - Tennis Courts |
| MON 4/29 | 3:45 PM | League | Haddam-Killingworth | Westbrook | Haddam Killingworth High School (HK) - HKHS Tennis Courts |
| MON 4/29 | 3:45 PM | League | Hall | Northwest Catholic | Hall High School - Tennis Courts |
| MON 4/29 | 3:45 PM | League | Ledyard | Killingly | Ledyard High School - Tennis Courts |
| MON 4/29 | 3:45 PM | League | Litchfield | Wamogo | Litchfield High School - LHS Tennis Courts |
| MON 4/29 | 3:45 PM | League | Lyman Memorial | Windham / Windham Tech | Lyman Memorial High School - Tennis Courts |
| MON 4/29 | 3:45 PM | League | Maloney | Plainville | Maloney High School - Tennis Courts |
| MON 4/29 | 3:45 PM | League | Manchester | South Windsor | Manchester Tennis Courts - Manchester |
| MON 4/29 | 3:45 PM | League | New Fairfield | Bunnell | New Fairfield High School - Tennis Courts |
| MON 4/29 | 3:45 PM | League | New Milford | Brookfield | New Milford High School - Tennis Courts - NMHS |
| MON 4/29 | 3:45 PM | League | Nonnewaug | Northwestern | Nonnewaug High School - Tennis Courts |
| MON 4/29 | 3:45 PM | League | Platt | Berlin | Platt High School - Tennis Court |
| MON 4/29 | 3:45 PM | League | Daniel Hand | Guilford | Polson Middle School, Madison - Polson Tennis Courts/DHHS Campus |
| MON 4/29 | 3:45 PM | League | Portland | Morgan | Portland High School - Tennis Courts |
| MON 4/29 | 3:45 PM | League | Sheehan | Mercy | Sheehan High School - Sheehan HS Tennis Courts |
| MON 4/29 | 3:45 PM | League | Shelton | Jonathan Law | Shelton High School - Tennis Courts |
| MON 4/29 | 3:45 PM | League | Simsbury | Avon | Simsbury High School - Tennis Courts |
| MON 4/29 | 3:45 PM | League | Southington | Windsor | Southington High School - Tennis Courts |
| MON 4/29 | 3:45 PM | League | Thomaston | Gilbert | Thomaston High School - Nystrom Park |
| MON 4/29 | 3:45 PM | League | Housatonic Regional | Shepaug Valley | Town Field - Town Tennis Courts |
| MON 4/29 | 3:45 PM | League | Valley Regional | Coginchaug | Valley Regional High School - Tennis Courts |
| MON 4/29 | 3:45 PM | League | Notre Dame-Fairfield | Weston | Veteran's Park - Bridgeport - Tennis Courts |
| MON 4/29 | 3:45 PM | League | Wethersfield | Rocky Hill | Wethersfield High School - Tennis Courts |
| MON 4/29 | 3:45 PM | League | Masuk | Immaculate | Wolfe Park - Tennis Courts |
| MON 4/29 | 3:45 PM | Non-League | Bolton | Ellington | Bolton High School - BHS Tennis Courts |
| MON 4/29 | 3:45 PM | Non-League | Lyman Hall | Wilcox Tech | Doolittle Park - Doolittle Tennis Courts |
| MON 4/29 | 4:00 PM | League | Sacred Heart Academy | Lauralton Hall | Albertus Magnus - Tennis Courts |
| MON 4/29 | 4:00 PM | League | Brien McMahon | New Canaan | Brien McMahon High School - Tennis Courts |
| MON 4/29 | 4:00 PM | League | Coventry | Windsor Locks | Coventry High School - tennis courts |
| MON 4/29 | 4:00 PM | League | Danbury | Norwalk | Danbury High School - DHS Tennis Courts |
| MON 4/29 | 4:00 PM | League | Fairfield Ludlowe | Ridgefield | Fairfield Ludlowe High School - Tennis Courts |
| MON 4/29 | 4:00 PM | League | Grasso Tech | Abbott Tech | Fitch High School - Tennis Courts |
| MON 4/29 | 4:00 PM | League | Newington | New Britain | Newington High School - Tennis Courts |
| MON 4/29 | 4:00 PM | League | St. Paul Catholic | Wolcott | Page Park - Tennis Courts |
| MON 4/29 | 4:00 PM | League | Stamford | Trumbull | Stamford High School - SHS Tennis Courts |
| MON 4/29 | 4:00 PM | League | Staples | Fairfield Warde | Staples High School - Staples Tennis Courts |
| MON 4/29 | 4:15 PM | League | Greenwich | Darien | Greenwich High School - Tennis Courts |
| MON 4/29 | 4:30 PM | League | Bridgeport Central | Wilton | Bridgeport Central High School - Central High School Tennis Courts |
| MON 4/29 | 4:30 PM | League | Canton | Rockville | Mills Pond Park - Canton - Mills Pond |
| MON 4/29 | 4:45 PM | League | Pomperaug | Stratford | Edgewood Bath and Tennis Club - Edgewood Bath and Tennis Club |
| MON 4/29 | 5:15 PM | League | Grasso Tech | Abbott Tech | Fitch High School - Tennis Courts |
| MON 4/29 | 5:15 PM | League | Tolland | Enfield | Tolland High School - Tennis Courts |
| MON 4/29 | 5:50 PM | League | Thomaston | Gilbert | Thomaston High School - Nystrom Park |
| MON 4/29 | 6:45 PM | League | Woodstock Academy | East Lyme | Pomfret School - Field House |
| TUE 4/30 | 10:00 AM | League | Enfield | Plainville | Enfield High School - EHS TENNIS COURTS |
| TUE 4/30 | 3:45 PM | League | Berlin | Lewis Mills | Berlin High School - Tennis Courts |
| TUE 4/30 | 3:45 PM | League | Bristol Central | Hall | Bristol Central High School - Tennis Courts |
| TUE 4/30 | 3:45 PM | League | East Granby | Bolton | East Granby High School - EGHS Tennis Courts |
| TUE 4/30 | 3:45 PM | League | Platt Tech | Norwich Tech | Eisenhower Park - Eisenhower Park |
| TUE 4/30 | 3:45 PM | League | Foran | Cheshire | Foran High School - Richard A. Herman Memorial Tennis Courts |
| TUE 4/30 | 3:45 PM | League | Guilford | Amity | Guilford High School - GHS Tennis Courts |
| TUE 4/30 | 3:45 PM | League | Kennedy | Torrington | John F. Kennedy High School - Tennis Courts |
| TUE 4/30 | 3:45 PM | League | North Branford | Morgan | North Branford High School - NBHS Tennis Courts |
| TUE 4/30 | 3:45 PM | League | Simsbury | Rocky Hill | Simsbury High School - Tennis Courts |
| TUE 4/30 | 3:45 PM | League | St. Bernard | Fitch | St. Bernard School - Tennis Courts |
| TUE 4/30 | 3:45 PM | League | Stonington | Montville | Stonington High School - SHS Tennis Courts |
| TUE 4/30 | 3:45 PM | League | Thomaston | Northwestern | Thomaston High School - Nystrom Park |
| TUE 4/30 | 3:45 PM | League | Wethersfield | Suffield | Wethersfield High School - Tennis Courts |
| TUE 4/30 | 3:45 PM | League | Wilcox Tech | Prince Tech | Wilcox Tech - Tennis Courts |
| TUE 4/30 | 3:45 PM | Non-League | Bethel | Nonnewaug | Bethel High School - BHS Tennis Courts |
| TUE 4/30 | 3:45 PM | Non-League | Litchfield | Watertown | Litchfield High School - LHS Tennis Courts |
| TUE 4/30 | 3:45 PM | Non-League | New London | Grasso Tech | New London High School - NLHS Tennis Courts |
| TUE 4/30 | 4:00 PM | League | Danbury | Ridgefield | Danbury High School - DHS Tennis Courts |
| TUE 4/30 | 4:00 PM | League | Fairfield Warde | Darien | Fairfield Warde High School - Blake Courts |
| TUE 4/30 | 4:00 PM | League | Norwalk | Trumbull | Grassroots Tennis and Education - Grassroots Tennis Courts |
| TUE 4/30 | 4:00 PM | League | Canton | Ellington | Mills Pond Park - Canton - Mills Pond |
| TUE 4/30 | 4:00 PM | League | Old Saybrook | Cromwell | Old Saybrook High School - Old Saybrook Tennis Courts |
| TUE 4/30 | 4:00 PM | League | Staples | Fairfield Ludlowe | Staples High School - Staples Tennis Courts |
| TUE 4/30 | 4:00 PM | League | Westhill | New Canaan | Westhill High School - Westhill Tennis Courts |
| TUE 4/30 | 4:15 PM | League | Greenwich | Stamford | Greenwich High School - Tennis Courts |
| TUE 4/30 | 4:15 PM | League | New Fairfield | Newtown | New Fairfield High School - Tennis Courts |
| TUE 4/30 | 5:00 PM | League | Bridgeport Central | Brien McMahon | Bridgeport Central High School - Central High School Tennis Courts |
| TUE 4/30 | 5:00 PM | League | Rockville | Coventry | Rockville High School - RHS Tennis Courts |
| WED 5/1 | 3:30 PM | League | Seymour | Torrington | Seymour High School - Tennis |
| WED 5/1 | 3:30 PM | League | Westbrook | Old Saybrook | Westbrook High School - Westbrook HS / MS Tennis Courts |
| WED 5/1 | 3:30 PM | League | Wolcott | Kennedy | Wolcott High School - WHS Tennis Courts |
| WED 5/1 | 3:30 PM | Scrimmage | Woodland | Naugatuck, Watertown | Woodland High School - Tennis Courts |
| WED 5/1 | 3:45 PM | League | Branford | Sacred Heart Academy | Branford High School - Tennis Courts |
| WED 5/1 | 3:45 PM | League | Brookfield | Masuk | Brookfield High School - BHS Tennis Courts |
| WED 5/1 | 3:45 PM | League | Bunnell | Joel Barlow | Bunnell HS - Bunnell Tennis Courts |
| WED 5/1 | 3:45 PM | League | Bloomfield | New Britain | Carmen Arace - Tennis Courts |
| WED 5/1 | 3:45 PM | League | Lyman Hall | Sheehan | Doolittle Park - Doolittle Tennis Courts |
| WED 5/1 | 3:45 PM | League | East Hartford | E.O. Smith | East Hartford High School - Tennis Courts |
| WED 5/1 | 3:45 PM | League | Pomperaug | Notre Dame-Fairfield | Edgewood Bath and Tennis Club - Edgewood Bath and Tennis Club |
| WED 5/1 | 3:45 PM | League | Stratford | Newtown | Flood Middle School - Flood MS Tennis Courts |
| WED 5/1 | 3:45 PM | League | Glastonbury | Hall | Glastonbury High School - Tennis Courts |
| WED 5/1 | 3:45 PM | League | Jonathan Law | Foran | Jonathan Law High School - Tennis Courts |
| WED 5/1 | 3:45 PM | League | Killingly | St. Bernard | Killingly High School - Tennis Courts |
| WED 5/1 | 3:45 PM | League | Montville | New London | Leary Park - Tennis Courts |
| WED 5/1 | 3:45 PM | League | Old Lyme | Valley Regional | Lyme-Old Lyme High School - Tennis Courts |
| WED 5/1 | 3:45 PM | League | Maloney | Bristol Eastern | Maloney High School - Tennis Courts |
| WED 5/1 | 3:45 PM | League | Manchester | Tolland | Manchester Tennis Courts - Manchester |
| WED 5/1 | 3:45 PM | League | Nonnewaug | Gilbert | Nonnewaug High School - Tennis Courts |
| WED 5/1 | 3:45 PM | League | Northwestern | Shepaug Valley | Northwestern Regional H.S. - Tennis Courts |
| WED 5/1 | 3:45 PM | League | Plainville | Middletown | Plainville High School - PHS Tennis Courts |
| WED 5/1 | 3:45 PM | League | Platt | Bristol Central | Platt High School - Tennis Court |
| WED 5/1 | 3:45 PM | League | Portland | Cromwell | Portland High School - Tennis Courts |
| WED 5/1 | 3:45 PM | League | Norwich Free Academy | Woodstock Academy | Rec Fields - Armstrong Tennis Courts |
| WED 5/1 | 3:45 PM | League | Rocky Hill | Windsor | Rocky Hill High School - tennis courts |
| WED 5/1 | 3:45 PM | League | Immaculate | Bethel | Rogers Park (Danbury, CT) - Tennis Courts |
| WED 5/1 | 3:45 PM | League | Simsbury | Conard | Simsbury High School - Tennis Courts |
| WED 5/1 | 3:45 PM | League | Housatonic Regional | Litchfield | Town Field - Town Tennis Courts |
| WED 5/1 | 3:45 PM | League | Wamogo | Thomaston | Wamogo Regional High School - Tennis Courts |
| WED 5/1 | 3:45 PM | League | West Haven | Shelton | West Haven High School - West Haven Tennis Courts |
| WED 5/1 | 3:45 PM | League | Weston | New Milford | Weston High School - WHS Tennis Courts |
| WED 5/1 | 3:45 PM | League | East Catholic | RHAM | Wickham Park - Wickham Park |
| WED 5/1 | 3:45 PM | Non-League | Bolton | Windham / Windham Tech | Bolton High School - BHS Tennis Courts |
| WED 5/1 | 3:45 PM | Non-League | East Haven | Wilcox Tech | East Haven High School - Tennis Court |
| WED 5/1 | 4:00 PM | League | Coginchaug | East Hampton | Coginchaug Regional High School - Tennis Courts @ CRHS |
| WED 5/1 | 4:00 PM | League | Prince Tech | Abbott Tech | Elizabeth Park - Elizabeth Park Courts 1,2,3,4,5,6 |
| WED 5/1 | 4:00 PM | League | Farmington | Northwest Catholic | Farmington High School - Farmington High School |
| WED 5/1 | 4:00 PM | League | Ridgefield | Westhill | Ridgefield High School - RHS Tennis Courts |
| WED 5/1 | 4:00 PM | League | St. Joseph | Wilton | St. Joseph High School - Tennis Courts |
| WED 5/1 | 4:00 PM | League | Staples | Darien | Staples High School - Staples Tennis Courts |
| WED 5/1 | 4:00 PM | Non-League | Newington | Windsor Locks | Newington High School - Tennis Courts |
| WED 5/1 | 4:15 PM | League | South Windsor | Enfield | South Windsor High School - Wapping Tennis Courts |
| WED 5/1 | 4:30 PM | League | St. Paul Catholic | Crosby | Bristol Eastern High School - Tennis Court |
| WED 5/1 | 5:30 PM | League | Waterford | East Lyme | Waterford High School - Tennis Courts - WHS |
| THU 5/2 | 2:30 PM | League | Wilby | Holy Cross | Wilby High School - Dave Krill Tennis Courts at WHS |
| THU 5/2 | 3:30 PM | League | Naugatuck | Ansonia | Naugatuck High School - Tennis Courts |
| THU 5/2 | 3:30 PM | League | Newtown | Joel Barlow | Newtown High School - NHS Tennis Courts |
| THU 5/2 | 3:30 PM | League | Wolcott | Crosby | Wolcott High School - WHS Tennis Courts |
| THU 5/2 | 3:45 PM | League | Bethel | Bunnell | Bethel High School - BHS Tennis Courts |
| THU 5/2 | 3:45 PM | League | Platt Tech | Abbott Tech | Eisenhower Park - Eisenhower Park |
| THU 5/2 | 3:45 PM | League | Prince Tech | Grasso Tech | Elizabeth Park - Elizabeth Park Courts 1,2,3,4,5,6 |
| THU 5/2 | 3:45 PM | League | Granby Memorial | Ellington | Granby Memorial High School - Tennis Courts |
| THU 5/2 | 3:45 PM | League | Guilford | Branford | Guilford High School - GHS Tennis Courts |
| THU 5/2 | 3:45 PM | League | Hamden | Career Magnet | Hamden Middle School - Tennis Courts |
| THU 5/2 | 3:45 PM | League | Killingly | Waterford | Killingly High School - Tennis Courts |
| THU 5/2 | 3:45 PM | League | Ledyard | Montville | Ledyard High School - Tennis Courts |
| THU 5/2 | 3:45 PM | League | Lewis Mills | Bristol Eastern | Lewis Mills High School - Tennis Courts |
| THU 5/2 | 3:45 PM | League | Lyman Memorial | Windham / Windham Tech | Lyman Memorial High School - Tennis Courts |
| THU 5/2 | 3:45 PM | League | New Fairfield | Stratford | New Fairfield High School - Tennis Courts |
| THU 5/2 | 3:45 PM | League | North Branford | Haddam-Killingworth | North Branford High School - NBHS Tennis Courts |
| THU 5/2 | 3:45 PM | League | Norwich Tech | Wilcox Tech | Norwich Technical High School - NTHS Outdoor Athletic Complex |
| THU 5/2 | 3:45 PM | League | Stonington | Fitch | Stonington High School - SHS Tennis Courts |
| THU 5/2 | 3:45 PM | League | Westbrook | East Hampton | Westbrook High School - Westbrook HS / MS Tennis Courts |
| THU 5/2 | 3:45 PM | League | Windsor Locks | Bolton | Windsor Locks High School - Tennis Court |
| THU 5/2 | 4:00 PM | League | Darien | Danbury | Darien High School - DHS Tennis Courts |
| THU 5/2 | 4:00 PM | League | Fairfield Ludlowe | Stamford | Fairfield Ludlowe High School - Tennis Courts |
| THU 5/2 | 4:00 PM | League | Fairfield Warde | Norwalk | Fairfield Warde High School - Blake Courts |
| THU 5/2 | 4:00 PM | League | Jonathan Law | Sacred Heart Academy | Jonathan Law High School - Tennis Courts |
| THU 5/2 | 4:00 PM | League | Canton | Suffield | Mills Pond Park - Canton - Mills Pond |
| THU 5/2 | 4:00 PM | League | Morgan | Old Saybrook | Morgan School - Tennis Courts |
| THU 5/2 | 4:00 PM | League | New Canaan | Bridgeport Central | New Canaan HS - NCHS Tennis Courts |
| THU 5/2 | 4:00 PM | League | Newington | Windsor | Newington High School - Tennis Courts |
| THU 5/2 | 4:00 PM | League | Ridgefield | Greenwich | Ridgefield High School - RHS Tennis Courts |
| THU 5/2 | 4:00 PM | League | St. Joseph | Brien McMahon | St. Joseph High School - Tennis Courts |
| THU 5/2 | 4:00 PM | League | Trumbull | Staples | Trumbull High School - Tennis Courts |
| THU 5/2 | 4:00 PM | League | Wilton | Westhill | Wilton High School - Allen Meadow |
| THU 5/2 | 4:15 PM | League | Wilby | St. Paul Catholic | Wilby High School - Dave Krill Tennis Courts at WHS |
| THU 5/2 | 4:30 PM | League | Coventry | E.O. Smith | Coventry High School - tennis courts |
| THU 5/2 | 5:00 PM | League | Holy Cross | St. Paul Catholic | Wilby High School - Dave Krill Tennis Courts at WHS |
| FRI 5/3 | 2:15 PM | League | Wolcott | Holy Cross | Wolcott High School - WHS Tennis Courts |
| FRI 5/3 | 2:30 PM | League | Gilbert | Wamogo | Walker Field - Tennis Courts |
| FRI 5/3 | 3:30 PM | League | Kennedy | Ansonia | John F. Kennedy High School - Tennis Courts |
| FRI 5/3 | 3:30 PM | League | Newtown | Notre Dame-Fairfield | Newtown High School - NHS Tennis Courts |
| FRI 5/3 | 3:30 PM | League | Wilby | Seymour | Wilby High School - Dave Krill Tennis Courts at WHS |
| FRI 5/3 | 3:30 PM | League | Woodland | Naugatuck | Woodland High School - Tennis Courts |
| FRI 5/3 | 3:45 PM | League | Amity | Jonathan Law | Amity Regional High School - Tennis Courts |
| FRI 5/3 | 3:45 PM | League | Berlin | Maloney | Berlin High School - Tennis Courts |
| FRI 5/3 | 3:45 PM | League | Bristol Central | E.O. Smith | Bristol Central High School - Tennis Courts |
| FRI 5/3 | 3:45 PM | League | Cheshire | Shelton | Cheshire High School - Tennis Courts |
| FRI 5/3 | 3:45 PM | League | Lauralton Hall | North Haven | Eisenhower Park - Eisenhower |
| FRI 5/3 | 3:45 PM | League | Fitch | Montville | Fitch High School - Main Tennis Courts |
| FRI 5/3 | 3:45 PM | League | Guilford | Mercy | Guilford High School - GHS Tennis Courts |
| FRI 5/3 | 3:45 PM | League | Haddam-Killingworth | East Hampton | Haddam Killingworth High School (HK) - HKHS Tennis Courts |
| FRI 5/3 | 3:45 PM | League | Hall | Farmington | Hall High School - Tennis Courts |
| FRI 5/3 | 3:45 PM | League | Middletown | Manchester | Middletown Tennis Courts - Beman Tennis Courts |
| FRI 5/3 | 3:45 PM | League | New Milford | Pomperaug | New Milford High School - Tennis Courts - NMHS |
| FRI 5/3 | 3:45 PM | League | Northwestern | Thomaston | Northwestern Regional H.S. - Tennis Courts |
| FRI 5/3 | 3:45 PM | League | Norwich Tech | New London | Norwich Technical High School - NTHS Outdoor Athletic Complex |
| FRI 5/3 | 3:45 PM | League | Plainville | Platt | Plainville High School - PHS Tennis Courts |
| FRI 5/3 | 3:45 PM | League | Daniel Hand | Sheehan | Polson Middle School, Madison - Polson Tennis Courts/DHHS Campus |
| FRI 5/3 | 3:45 PM | League | RHAM | East Catholic | RHAM High School - Tennis Courts |
| FRI 5/3 | 3:45 PM | League | Rocky Hill | Southington | Rocky Hill High School - tennis courts |
| FRI 5/3 | 3:45 PM | League | Immaculate | Brookfield | Rogers Park (Danbury, CT) - Tennis Courts |
| FRI 5/3 | 3:45 PM | League | Shepaug Valley | Litchfield | Shepaug Valley High School - Shepaug Valley Tennis Courts |
| FRI 5/3 | 3:45 PM | League | South Windsor | Northwest Catholic | South Windsor High School - Wapping Tennis Courts |
| FRI 5/3 | 3:45 PM | League | St. Bernard | Norwich Free Academy | St. Bernard School - Tennis Courts |
| FRI 5/3 | 3:45 PM | League | Housatonic Regional | Nonnewaug | Town Field - Town Tennis Courts |
| FRI 5/3 | 3:45 PM | League | West Haven | Lyman Hall | West Haven High School - West Haven Tennis Courts |
| FRI 5/3 | 3:45 PM | League | Wethersfield | Avon | Wethersfield High School - Tennis Courts |
| FRI 5/3 | 3:45 PM | League | Windsor | New Britain | Windsor High School - WHS Tennis Courts |
| FRI 5/3 | 3:45 PM | League | Masuk | Weston | Wolfe Park - Tennis Courts |
| FRI 5/3 | 3:45 PM | Non-League | Platt Tech | Foran | Eisenhower Park - Eisenhower Park |
| FRI 5/3 | 4:00 PM | League | Coventry | Granby Memorial | Coventry High School - tennis courts |
| FRI 5/3 | 4:00 PM | League | Lyman Memorial | Ledyard | Lyman Memorial High School - Tennis Courts |
| FRI 5/3 | 4:00 PM | League | North Branford | Portland | North Branford High School - NBHS Tennis Courts |
| FRI 5/3 | 4:00 PM | League | BulkeleyHMTCA/Weaver | East Granby | Weaver High School - Tennis Courts |
| FRI 5/3 | 4:30 PM | League | Watertown | St. Paul Catholic | Crestbrook Park - Crestbrook Park Tennis Courts |
| FRI 5/3 | 4:30 PM | League | Gilbert | Wamogo | Rowley Field - Tennis Courts |
| FRI 5/3 | 5:15 PM | League | Conard | Enfield | Conard High School - Tennis Courts |
| SAT 5/4 | 10:00 AM | League | Southington | Newington | Southington High School - Tennis Courts |
| SAT 5/4 | 10:00 AM | Non-League | North Branford | East Haven | North Branford High School - NBHS Tennis Courts |
| SAT 5/4 | 10:30 AM | League | Ansonia | Torrington | Ansonia High School - Woodland |
| SAT 5/4 | 11:00 AM | League | Guilford | Fitch | Guilford High School - GHS Tennis Courts |
| SAT 5/4 | 11:00 AM | League | Stonington | Windham / Windham Tech | Stonington High School - SHS Tennis Courts |
| SAT 5/4 | 12:00 PM | League | Ansonia | Torrington | Ansonia High School - Woodland |
| SAT 5/4 | 5:00 PM | League | Jonathan Law | Platt Tech | Jonathan Law High School - Tennis Courts |
| SAT 5/4 | 9:00 AM | Non-League | Old Lyme | Waterford | Lyme-Old Lyme High School - Tennis Courts |
| MON 5/6 | 2:00 PM | League | E.O. Smith | Southington | E.O. Smith High School - Tennis Courts |
| MON 5/6 | 2:00 PM | League | Lyman Memorial | Montville | Lyman Memorial High School - Tennis Courts |
| MON 5/6 | 3:30 PM | League | Crosby | Wilby | Crosby High School - CHS Tennis. Courts |
| MON 5/6 | 3:30 PM | League | Kennedy | Holy Cross | John F. Kennedy High School - Tennis Courts |
| MON 5/6 | 3:30 PM | League | Newtown | New Milford | Newtown High School - NHS Tennis Courts |
| MON 5/6 | 3:45 PM | League | Amity | Guilford | Amity Regional High School - Tennis Courts |
| MON 5/6 | 3:45 PM | League | Bristol Eastern | Plainville | Bristol Eastern High School - Tennis Court |
| MON 5/6 | 3:45 PM | League | Brookfield | Bethel | Brookfield High School - BHS Tennis Courts |
| MON 5/6 | 3:45 PM | League | Bloomfield | Manchester | Carmen Arace - Tennis Courts |
| MON 5/6 | 3:45 PM | League | Cheshire | Daniel Hand | Cheshire High School - Tennis Courts |
| MON 5/6 | 3:45 PM | League | Conard | Wethersfield | Conard High School - Tennis Courts |
| MON 5/6 | 3:45 PM | League | Watertown | Naugatuck | Crestbrook Park - Crestbrook Park Tennis Courts |
| MON 5/6 | 3:45 PM | League | Lyman Hall | North Haven | Doolittle Park - Doolittle Tennis Courts |
| MON 5/6 | 3:45 PM | League | Pomperaug | Masuk | Edgewood Bath and Tennis Club - Edgewood Bath and Tennis Club |
| MON 5/6 | 3:45 PM | League | Career Magnet | Lauralton Hall | Edgewood Park - Tennis Courts |
| MON 5/6 | 3:45 PM | League | Foran | Shelton | Foran High School - Richard A. Herman Memorial Tennis Courts |
| MON 5/6 | 3:45 PM | League | Haddam-Killingworth | Morgan | Haddam Killingworth High School (HK) - HKHS Tennis Courts |
| MON 5/6 | 3:45 PM | League | Farmington | East Hartford | Irving Robbins Middle School - Tennis Courts |
| MON 5/6 | 3:45 PM | League | Jonathan Law | West Haven | Jonathan Law High School - Tennis Courts |
| MON 5/6 | 3:45 PM | League | Maloney | RHAM | Maloney High School - Tennis Courts |
| MON 5/6 | 3:45 PM | League | New Britain | South Windsor | New Britain High School - tennis courts |
| MON 5/6 | 3:45 PM | League | New London | Killingly | New London High School - NLHS Tennis Courts |
| MON 5/6 | 3:45 PM | League | Northwestern | Gilbert | Northwestern Regional H.S. - Tennis Courts |
| MON 5/6 | 3:45 PM | League | Norwich Tech | Grasso Tech | Norwich Technical High School - NTHS Outdoor Athletic Complex |
| MON 5/6 | 3:45 PM | League | Platt | Lewis Mills | Platt High School - Tennis Court |
| MON 5/6 | 3:45 PM | League | Portland | Valley Regional | Portland High School - Tennis Courts |
| MON 5/6 | 3:45 PM | League | St. Bernard | Windham / Windham Tech | St. Bernard School - Tennis Courts |
| MON 5/6 | 3:45 PM | League | Avon | Glastonbury | Sycamore Park - Sycamore Park |
| MON 5/6 | 3:45 PM | League | Thomaston | Housatonic Regional | Thomaston High School - Nystrom Park |
| MON 5/6 | 3:45 PM | League | Northwest Catholic | Windsor | University of Saint Joseph - Tennis Courts |
| MON 5/6 | 3:45 PM | League | Notre Dame-Fairfield | New Fairfield | Veteran's Park - Bridgeport - Tennis Courts |
| MON 5/6 | 3:45 PM | League | Wamogo | Shepaug Valley | Wamogo Regional High School - Tennis Courts |
| MON 5/6 | 3:45 PM | League | Westbrook | Cromwell | Westbrook High School - Westbrook HS / MS Tennis Courts |
| MON 5/6 | 3:45 PM | League | Weston | Immaculate | Weston High School - WHS Tennis Courts |
| MON 5/6 | 3:45 PM | League | East Catholic | Berlin | Wickham Park - Wickham Park |
| MON 5/6 | 3:45 PM | League | Windsor Locks | Coventry | Windsor Locks High School - Tennis Court |
| MON 5/6 | 3:45 PM | League | Wolcott | Ansonia | Wolcott High School - WHS Tennis Courts |
| MON 5/6 | 3:45 PM | Non-League | Wilcox Tech | East Haven | Wilcox Tech - Tennis Courts |
| MON 5/6 | 4:00 PM | League | Sacred Heart Academy | Branford | Albertus Magnus - Tennis Courts |
| MON 5/6 | 4:00 PM | League | Coginchaug | North Branford | Coginchaug Regional High School - Tennis Courts @ CRHS |
| MON 5/6 | 4:00 PM | League | Danbury | Staples | Danbury High School - DHS Tennis Courts |
| MON 5/6 | 4:00 PM | League | Darien | Fairfield Ludlowe | Darien High School - DHS Tennis Courts |
| MON 5/6 | 4:00 PM | League | Ellington | Suffield | Ellington High School - Tennis Courts |
| MON 5/6 | 4:00 PM | League | Norwalk | Greenwich | Grassroots Tennis and Education - Grassroots Tennis Courts |
| MON 5/6 | 4:00 PM | League | Lyman Memorial | Montville | Lyman Memorial High School - Tennis Courts |
| MON 5/6 | 4:00 PM | League | New Canaan | St. Joseph | New Canaan HS - NCHS Tennis Courts |
| MON 5/6 | 4:00 PM | League | Old Saybrook | Old Lyme | Old Saybrook High School - Old Saybrook Tennis Courts |
| MON 5/6 | 4:00 PM | League | Trumbull | Ridgefield | Trumbull High School - Tennis Courts |
| MON 5/6 | 4:00 PM | League | Westhill | Bridgeport Central | Westhill High School - Westhill Tennis Courts |
| MON 5/6 | 4:00 PM | League | Wilton | Brien McMahon | Wilton High School - Tennis Courts |
| MON 5/6 | 4:30 PM | League | Enfield | Newington | Enfield High School - EHS TENNIS COURTS |
| MON 5/6 | 4:30 PM | League | Fairfield Warde | Stamford | Fairfield Warde High School - Blake Courts |
| MON 5/6 | 4:30 PM | League | Joel Barlow | Stratford | Joel Barlow High School - Tennis Courts |
| MON 5/6 | 4:30 PM | League | Litchfield | Nonnewaug | Litchfield High School - LHS Tennis Courts |
| MON 5/6 | 5:00 PM | League | Mercy | Hamden | Wesleyan University - Tennis Courts |
| MON 5/6 | 6:45 PM | League | Woodstock Academy | Waterford | Pomfret School - Field House |
| TUE 5/7 | 3:00 PM | League | East Catholic | Enfield | Wickham Park - Wickham Park |
| TUE 5/7 | 3:15 PM | League | Tolland | Middletown | Tolland High School - Tennis Courts |
| TUE 5/7 | 3:30 PM | League | Bristol Eastern | Conard | Bristol Eastern High School - Tennis Court |
| TUE 5/7 | 3:30 PM | League | Newtown | Masuk | Newtown High School - NHS Tennis Courts |
| TUE 5/7 | 3:30 PM | League | Wolcott | Torrington | Wolcott High School - WHS Tennis Courts |
| TUE 5/7 | 3:45 PM | League | Abbott Tech | Prince Tech | Abbott V-T School - Abbott Tech Tennis Complex |
| TUE 5/7 | 3:45 PM | League | Bolton | Suffield | Bolton High School - BHS Tennis Courts |
| TUE 5/7 | 3:45 PM | League | Watertown | Ansonia | Crestbrook Park - Crestbrook Park Tennis Courts |
| TUE 5/7 | 3:45 PM | League | East Lyme | Norwich Free Academy | East Lyme High School - Tennis Courts |
| TUE 5/7 | 3:45 PM | League | Platt Tech | Wilcox Tech | Eisenhower Park - Eisenhower Park |
| TUE 5/7 | 3:45 PM | League | Haddam-Killingworth | East Hampton | Haddam Killingworth High School (HK) - HKHS Tennis Courts |
| TUE 5/7 | 3:45 PM | League | Ledyard | Stonington | Ledyard High School - Tennis Courts |
| TUE 5/7 | 3:45 PM | League | Lewis Mills | Maloney | Lewis Mills High School - Tennis Courts |
| TUE 5/7 | 3:45 PM | League | Manchester | Northwest Catholic | Manchester Tennis Courts - Manchester |
| TUE 5/7 | 3:45 PM | League | Morgan | Valley Regional | Morgan School - Tennis Courts |
| TUE 5/7 | 3:45 PM | League | New Milford | New Fairfield | New Milford High School - Tennis Courts - NMHS |
| TUE 5/7 | 3:45 PM | League | Nonnewaug | Housatonic Regional | Nonnewaug High School - Tennis Courts |
| TUE 5/7 | 3:45 PM | League | Rocky Hill | Hall | Rocky Hill High School - tennis courts |
| TUE 5/7 | 3:45 PM | League | Sheehan | East Haven | Sheehan High School - Sheehan HS Tennis Courts |
| TUE 5/7 | 3:45 PM | League | Shelton | Mercy | Shelton High School - Tennis Courts |
| TUE 5/7 | 3:45 PM | League | St. Bernard | New London | St. Bernard School - Tennis Courts |
| TUE 5/7 | 3:45 PM | League | Cromwell | North Branford | Watrous park - Watrous park |
| TUE 5/7 | 3:45 PM | League | Weston | Brookfield | Weston High School - WHS Tennis Courts |
| TUE 5/7 | 3:45 PM | Non-League | Windsor Locks | Windham / Windham Tech | Windsor Locks High School - Tennis Court |
| TUE 5/7 | 4:00 PM | League | Bridgeport Central | Danbury | Bridgeport Central High School - Central High School Tennis Courts |
| TUE 5/7 | 4:00 PM | League | Brien McMahon | Fairfield Warde | Brien McMahon High School - Tennis Courts |
| TUE 5/7 | 4:00 PM | League | Coventry | Canton | Coventry High School - tennis courts |
| TUE 5/7 | 4:00 PM | League | Fairfield Ludlowe | Wilton | Fairfield Ludlowe High School - Tennis Courts |
| TUE 5/7 | 4:00 PM | League | New Canaan | Trumbull | New Canaan HS - NCHS Tennis Courts |
| TUE 5/7 | 4:00 PM | League | Ridgefield | Darien | Ridgefield High School - RHS Tennis Courts |
| TUE 5/7 | 4:00 PM | League | Stamford | Norwalk | Stamford High School - SHS Tennis Courts |
| TUE 5/7 | 4:00 PM | League | Staples | St. Joseph | Staples High School - Staples Tennis Courts |
| TUE 5/7 | 4:15 PM | League | Greenwich | Westhill | Greenwich High School - Tennis Courts |
| TUE 5/7 | 4:30 PM | League | Woodland | St. Paul Catholic | Woodland High School - Tennis Courts |
| TUE 5/7 | 4:45 PM | League | Stratford | Bunnell | Flood Middle School - Flood MS Tennis Courts |
| TUE 5/7 | 5:00 PM | League | Guilford | Cheshire | Guilford High School - GHS Tennis Courts |
| TUE 5/7 | 5:00 PM | League | Simsbury | Bristol Central | Simsbury High School - Tennis Courts |
| TUE 5/7 | 5:00 PM | League | Waterford | Montville | Waterford High School - Tennis Courts - WHS |
| TUE 5/7 | 6:15 PM | League | Woodstock Academy | Lyman Memorial | Pomfret School - Outside Tennis Courts |
| WED 5/8 | 2:00 PM | League | Bolton | Granby Memorial | Magic Lincer Tennis- Manchester - Magic Lincer Tennis Academy- Manchester |
| WED 5/8 | 2:45 PM | League | New London | Lyman Memorial | New London High School - NLHS Tennis Courts |
| WED 5/8 | 3:00 PM | League | St. Paul Catholic | Naugatuck | Page Park - Tennis Courts |
| WED 5/8 | 3:30 PM | League | Ansonia | Crosby | Nolan Field-Ansonia - Nolan Field- Tennis Courts |
| WED 5/8 | 3:30 PM | League | Seymour | Kennedy | Seymour High School - Tennis |
| WED 5/8 | 3:30 PM | League | Notre Dame-Fairfield | Joel Barlow | Veteran's Park - Bridgeport - Tennis Courts |
| WED 5/8 | 3:30 PM | League | Wilby | Torrington | Wilby High School - Dave Krill Tennis Courts at WHS |
| WED 5/8 | 3:30 PM | League | Wolcott | Watertown | Wolcott High School - WHS Tennis Courts |
| WED 5/8 | 3:30 PM | League | Woodland | Holy Cross | Woodland High School - Tennis Courts |
| WED 5/8 | 3:45 PM | League | Amity | Daniel Hand | Amity Regional High School - Tennis Courts |
| WED 5/8 | 3:45 PM | League | Bristol Central | Maloney | Bristol Central High School - Tennis Courts |
| WED 5/8 | 3:45 PM | League | Bristol Eastern | Platt | Bristol Eastern High School - Tennis Court |
| WED 5/8 | 3:45 PM | League | Conard | Glastonbury | Conard High School - Tennis Courts |
| WED 5/8 | 3:45 PM | League | East Hartford | Tolland | East Hartford High School - Tennis Courts |
| WED 5/8 | 3:45 PM | League | Pomperaug | Immaculate | Edgewood Bath and Tennis Club - Edgewood Bath and Tennis Club |
| WED 5/8 | 3:45 PM | League | Lauralton Hall | Branford | Eisenhower Park - Eisenhower Park |
| WED 5/8 | 3:45 PM | League | Hamden | Foran | Hamden Middle School - Tennis Courts |
| WED 5/8 | 3:45 PM | League | Jonathan Law | Sheehan | Jonathan Law High School - Tennis Courts |
| WED 5/8 | 3:45 PM | League | Lewis Mills | Plainville | Lewis Mills High School - Tennis Courts |
| WED 5/8 | 3:45 PM | League | Middletown | Berlin | Middletown Tennis Courts - Beman Tennis Courts |
| WED 5/8 | 3:45 PM | League | New Britain | Windsor | New Britain High School - tennis courts |
| WED 5/8 | 3:45 PM | League | Nonnewaug | Thomaston | Nonnewaug High School - Tennis Courts |
| WED 5/8 | 3:45 PM | League | North Branford | Westbrook | North Branford High School - NBHS Tennis Courts |
| WED 5/8 | 3:45 PM | League | Northwestern | Litchfield | Northwestern Regional H.S. - Tennis Courts |
| WED 5/8 | 3:45 PM | League | Old Saybrook | Portland | Old Saybrook High School - Old Saybrook Tennis Courts |
| WED 5/8 | 3:45 PM | League | Norwich Free Academy | Ledyard | Rec Fields - Armstrong Tennis Courts |
| WED 5/8 | 3:45 PM | League | Rockville | Ellington | Rockville High School - RHS Tennis Courts |
| WED 5/8 | 3:45 PM | League | Shepaug Valley | Gilbert | Shepaug Valley High School - Shepaug Valley Tennis Courts |
| WED 5/8 | 3:45 PM | League | South Windsor | RHAM | South Windsor High School - Wapping Tennis Courts |
| WED 5/8 | 3:45 PM | League | Northwest Catholic | Avon | University of Saint Joseph - Tennis Courts |
| WED 5/8 | 3:45 PM | League | West Haven | East Haven | West Haven High School - West Haven Tennis Courts |
| WED 5/8 | 3:45 PM | League | Wethersfield | Farmington | Wethersfield High School - Tennis Courts |
| WED 5/8 | 3:45 PM | League | Wilcox Tech | Grasso Tech | Wilcox Tech - Tennis Courts |
| WED 5/8 | 3:45 PM | Non-League | Old Lyme | Stonington | Lyme-Old Lyme High School - Tennis Courts |
| WED 5/8 | 4:00 PM | League | Cromwell | East Hampton | Watrous park - Watrous park |
| WED 5/8 | 4:00 PM | League | Westhill | St. Joseph | Westhill High School - Westhill Tennis Courts |
| WED 5/8 | 4:30 PM | League | Brien McMahon | Darien | Brien McMahon High School - Tennis Courts |
| THU 5/9 | 3:30 PM | League | Kennedy | Woodland | John F. Kennedy High School - Tennis Courts |
| THU 5/9 | 3:30 PM | League | Naugatuck | Crosby | Naugatuck High School - Tennis Courts |
| THU 5/9 | 3:30 PM | League | Suffield | Granby Memorial | Suffield High School - Tennis Courts |
| THU 5/9 | 3:45 PM | League | Abbott Tech | Wilcox Tech | Abbott V-T School - Abbott Tech Tennis Complex |
| THU 5/9 | 3:45 PM | League | Bethel | Weston | Bethel High School - BHS Tennis Courts |
| THU 5/9 | 3:45 PM | League | Lyman Hall | Jonathan Law | Doolittle Park - Doolittle Tennis Courts |
| THU 5/9 | 3:45 PM | League | E.O. Smith | South Windsor | E.O. Smith High School - Tennis Courts |
| THU 5/9 | 3:45 PM | League | Platt Tech | Grasso Tech | Eisenhower Park - Eisenhower Park |
| THU 5/9 | 3:45 PM | League | Haddam-Killingworth | Portland | Haddam Killingworth High School (HK) - HKHS Tennis Courts |
| THU 5/9 | 3:45 PM | League | North Haven | Amity | North Haven Athletic Complex - Tennis Courts |
| THU 5/9 | 3:45 PM | League | Norwich Tech | Prince Tech | Norwich Technical High School - NTHS Outdoor Athletic Complex |
| THU 5/9 | 3:45 PM | League | Sheehan | Bristol Central | Sheehan High School - Sheehan HS Tennis Courts |
| THU 5/9 | 3:45 PM | League | St. Bernard | Lyman Memorial | St. Bernard School - Tennis Courts |
| THU 5/9 | 3:45 PM | League | Gilbert | Housatonic Regional | Walker Field - Tennis Courts |
| THU 5/9 | 3:45 PM | League | Windsor | Newington | Windsor High School - WHS Tennis Courts |
| THU 5/9 | 4:00 PM | League | East Granby | Coventry | East Granby High School - EGHS Tennis Courts |
| THU 5/9 | 4:00 PM | League | Fairfield Ludlowe | Trumbull | Fairfield Ludlowe High School - Tennis Courts |
| THU 5/9 | 4:00 PM | League | Canton | Windsor Locks | Mills Pond Park - Canton - Mills Pond |
| THU 5/9 | 4:00 PM | League | Old Saybrook | East Hampton | Old Saybrook High School - Old Saybrook Tennis Courts |
| THU 5/9 | 4:00 PM | League | Ridgefield | New Canaan | Ridgefield High School - RHS Tennis Courts |
| THU 5/9 | 4:00 PM | League | St. Joseph | Danbury | St. Joseph High School - Tennis Courts |
| THU 5/9 | 4:15 PM | League | Greenwich | Fairfield Warde | Greenwich High School - Tennis Courts |
| THU 5/9 | 4:15 PM | League | Wethersfield | Southington | Wethersfield High School - Tennis Courts |
| THU 5/9 | 4:15 PM | Non-League | Coginchaug | Westbrook | Coginchaug Regional High School - Tennis Courts @ CRHS |
| THU 5/9 | 4:30 PM | League | Bridgeport Central | Norwalk | Bridgeport Central High School - Central High School Tennis Courts |
| THU 5/9 | 4:30 PM | League | Stamford | Wilton | Stamford High School - SHS Tennis Courts |
| THU 5/9 | 4:30 PM | League | Staples | Westhill | Staples High School - Staples Tennis Courts |
| THU 5/9 | 6:00 PM | League | Canton | Bolton | Mills Pond Park - Canton - Mills Pond |
| THU 5/9 | 6:00 PM | League | Woodstock Academy | Norwich Free Academy | Pomfret School - Field House |
| FRI 5/10 | 3:30 PM | League | Crosby | Torrington | Crosby High School - CHS Tennis. Courts |
| FRI 5/10 | 3:30 PM | League | Holy Cross | Wolcott | Holy Cross - Tennis Courts |
| FRI 5/10 | 3:30 PM | League | Naugatuck | Woodland | Naugatuck High School - Tennis Courts |
| FRI 5/10 | 3:30 PM | League | Seymour | Wilby | Seymour High School - Tennis |
| FRI 5/10 | 3:45 PM | League | Berlin | Bristol Eastern | Berlin High School - Tennis Courts |
| FRI 5/10 | 3:45 PM | League | Bloomfield | Rocky Hill | Carmen Arace - Tennis Courts |
| FRI 5/10 | 3:45 PM | League | East Haven | Foran | East Haven High School - Tennis Court |
| FRI 5/10 | 3:45 PM | League | Career Magnet | Mercy | Edgewood Park - Tennis Courts |
| FRI 5/10 | 3:45 PM | League | Lauralton Hall | Guilford | Eisenhower Park - Eisenhower |
| FRI 5/10 | 3:45 PM | League | Enfield | East Hartford | Enfield High School - EHS TENNIS COURTS |
| FRI 5/10 | 3:45 PM | League | Fitch | Waterford | Fitch High School - Main Tennis Courts |
| FRI 5/10 | 3:45 PM | League | Haddam-Killingworth | Valley Regional | Haddam Killingworth High School (HK) - HKHS Tennis Courts |
| FRI 5/10 | 3:45 PM | League | Farmington | Conard | Irving Robbins Middle School - Tennis Courts |
| FRI 5/10 | 3:45 PM | League | Killingly | Windham / Windham Tech | Killingly High School - Tennis Courts |
| FRI 5/10 | 3:45 PM | League | Ledyard | New London | Ledyard High School - Tennis Courts |
| FRI 5/10 | 3:45 PM | League | Middletown | Platt | Middletown Tennis Courts - Beman Tennis Courts |
| FRI 5/10 | 3:45 PM | League | Nonnewaug | Shepaug Valley | Nonnewaug High School - Tennis Courts |
| FRI 5/10 | 3:45 PM | League | Plainville | Bristol Central | Plainville High School - PHS Tennis Courts |
| FRI 5/10 | 3:45 PM | League | RHAM | Manchester | RHAM High School - Tennis Courts |
| FRI 5/10 | 3:45 PM | League | Rockville | Canton | Rockville High School - RHS Tennis Courts |
| FRI 5/10 | 3:45 PM | League | Stonington | East Lyme | Stonington High School - SHS Tennis Courts |
| FRI 5/10 | 3:45 PM | League | Thomaston | Litchfield | Thomaston High School - Nystrom Park |
| FRI 5/10 | 3:45 PM | League | Northwest Catholic | Simsbury | University of Saint Joseph - Tennis Courts |
| FRI 5/10 | 3:45 PM | League | Wamogo | Northwestern | Wamogo Regional High School - Tennis Courts |
| FRI 5/10 | 3:45 PM | League | East Catholic | Tolland | Wickham Park - Wickham Park |
| FRI 5/10 | 3:45 PM | League | Windsor Locks | Granby Memorial | Windsor Locks High School - Tennis Court |
| FRI 5/10 | 3:45 PM | Non-League | Prince Tech | BulkeleyHMTCA/Weaver | Elizabeth Park - Elizabeth Park Courts 1,2,3,4,5,6 |
| FRI 5/10 | 4:00 PM | League | Sacred Heart Academy | Daniel Hand | Albertus Magnus - Tennis Courts |
| FRI 5/10 | 4:00 PM | League | Portland | North Branford | Portland High School - Tennis Courts |
| FRI 5/10 | 5:30 PM | League | Crosby | Torrington | Crosby High School - CHS Tennis. Courts |
| SAT 5/11 | 10:00 AM | Scrimmage | Woodland | Watertown, St. Paul Catholic, Ansonia, Kennedy | Woodland High School - Tennis Courts |
| SAT 5/11 | 12:00 AM | League | Old Lyme | East Hampton | Lyme-Old Lyme High School - Tennis Courts |
| SAT 5/11 | 9:00 AM | League | Manchester | E.O. Smith | Manchester Tennis Courts - Manchester |
| SAT 5/11 | 9:00 AM | League | Woodstock Academy | Montville | Pomfret School - Field House |
| SAT 5/11 | 9:00 AM | Non-League | Masuk | Seymour | Wolfe Park - Tennis Courts |
| MON 5/13 | 3:00 PM | League | Granby Memorial | East Granby | Granby Memorial High School - Tennis Courts |
| MON 5/13 | 3:30 PM | League | Kennedy | Torrington | John F. Kennedy High School - Tennis Courts |
| MON 5/13 | 3:30 PM | League | Seymour | Ansonia | Seymour High School - Tennis |
| MON 5/13 | 3:30 PM | League | Wilby | Crosby | Wilby High School - Dave Krill Tennis Courts at WHS |
| MON 5/13 | 3:30 PM | League | Wolcott | Naugatuck | Wolcott High School - WHS Tennis Courts |
| MON 5/13 | 3:45 PM | League | Bristol Central | Middletown | Bristol Central High School - Tennis Courts |
| MON 5/13 | 3:45 PM | League | Bristol Eastern | Lewis Mills | Bristol Eastern High School - Tennis Court |
| MON 5/13 | 3:45 PM | League | Brookfield | Pomperaug | Brookfield High School - BHS Tennis Courts |
| MON 5/13 | 3:45 PM | League | Bunnell | Notre Dame-Fairfield | Bunnell HS - Bunnell Tennis Courts |
| MON 5/13 | 3:45 PM | League | Cheshire | Lauralton Hall | Cheshire High School - Tennis Courts |
| MON 5/13 | 3:45 PM | League | Conard | Northwest Catholic | Conard High School - Tennis Courts |
| MON 5/13 | 3:45 PM | League | Watertown | Holy Cross | Crestbrook Park - Crestbrook Park Tennis Courts |
| MON 5/13 | 3:45 PM | League | E.O. Smith | Enfield | E.O. Smith High School - Tennis Courts |
| MON 5/13 | 3:45 PM | League | East Haven | Career Magnet | East Haven High School - Tennis Court |
| MON 5/13 | 3:45 PM | League | Platt Tech | Grasso Tech | Eisenhower Park - Eisenhower Park |
| MON 5/13 | 3:45 PM | League | Ellington | Nonnewaug | Ellington High School - Tennis Courts |
| MON 5/13 | 3:45 PM | League | Foran | Lyman Hall | Foran High School - Richard A. Herman Memorial Tennis Courts |
| MON 5/13 | 3:45 PM | League | Glastonbury | Avon | Glastonbury High School - Tennis Courts |
| MON 5/13 | 3:45 PM | League | Hamden | Shelton | Hamden Middle School - Tennis Courts |
| MON 5/13 | 3:45 PM | League | Joel Barlow | New Milford | Joel Barlow High School - Tennis Courts |
| MON 5/13 | 3:45 PM | League | Killingly | East Lyme | Killingly High School - Tennis Courts |
| MON 5/13 | 3:45 PM | League | Montville | Windham / Windham Tech | Leary Park - Tennis Courts |
| MON 5/13 | 3:45 PM | League | Maloney | Berlin | Maloney High School - Tennis Courts |
| MON 5/13 | 3:45 PM | League | Manchester | East Catholic | Manchester Tennis Courts - Manchester |
| MON 5/13 | 3:45 PM | League | North Haven | Daniel Hand | North Haven Athletic Complex - Tennis Courts |
| MON 5/13 | 3:45 PM | League | Northwestern | Canton | Northwestern Regional H.S. - Tennis Courts |
| MON 5/13 | 3:45 PM | League | Platt | Plainville | Platt High School - Tennis Court |
| MON 5/13 | 3:45 PM | League | Norwich Free Academy | Fitch | Rec Fields - Armstrong Tennis Courts |
| MON 5/13 | 3:45 PM | League | Sheehan | West Haven | Sheehan High School - Sheehan HS Tennis Courts |
| MON 5/13 | 3:45 PM | League | Simsbury | Farmington | Simsbury High School - Tennis Courts |
| MON 5/13 | 3:45 PM | League | South Windsor | East Hartford | South Windsor High School - Wapping Tennis Courts |
| MON 5/13 | 3:45 PM | League | Southington | Bloomfield | Southington High School - Tennis Courts |
| MON 5/13 | 3:45 PM | League | Tolland | RHAM | Tolland High School - Tennis Courts |
| MON 5/13 | 3:45 PM | League | Wamogo | Housatonic Regional | Wamogo Regional High School - Tennis Courts |
| MON 5/13 | 3:45 PM | League | Waterford | Ledyard | Waterford High School - Tennis Courts - WHS |
| MON 5/13 | 3:45 PM | League | Mercy | Branford | Wesleyan University - Tennis Courts |
| MON 5/13 | 3:45 PM | League | Wethersfield | New Britain | Wethersfield High School - Tennis Courts |
| MON 5/13 | 3:45 PM | Non-League | Abbott Tech | Immaculate | Abbott V-T School - Abbott Tech Tennis Complex |
| MON 5/13 | 3:45 PM | Non-League | Thomaston | Windsor Locks | Thomaston High School - Nystrom Park |
| MON 5/13 | 4:00 PM | League | Sacred Heart Academy | Jonathan Law | Albertus Magnus - Tennis Courts |
| MON 5/13 | 4:00 PM | League | Coventry | Rockville | Coventry High School - tennis courts |
| MON 5/13 | 4:00 PM | League | New London | St. Bernard | New London High School - NLHS Tennis Courts |
| MON 5/13 | 4:00 PM | League | Newington | Rocky Hill | Newington High School - Tennis Courts |
| MON 5/13 | 4:00 PM | League | Old Saybrook | North Branford | Old Saybrook High School - Old Saybrook Tennis Courts |
| MON 5/13 | 4:00 PM | League | BulkeleyHMTCA/Weaver | Windsor | Weaver High School - Tennis Courts |
| MON 5/13 | 4:00 PM | Non-League | Westbrook | East Hampton | Westbrook High School - Westbrook HS / MS Tennis Courts |
| MON 5/13 | 4:00 PM | Postseason | Darien | Staples | Darien High School - DHS Tennis Courts |
| MON 5/13 | 4:00 PM | Postseason | Fairfield Ludlowe | Wilton | Fairfield Ludlowe High School - Tennis Courts |
| MON 5/13 | 4:00 PM | Postseason | New Canaan | Fairfield Warde | New Canaan HS - NCHS Tennis Courts |
| MON 5/13 | 4:15 PM | League | Stonington | Woodstock Academy | Stonington High School - SHS Tennis Courts |
| MON 5/13 | 4:30 PM | Postseason | Greenwich | Westhill | Greenwich High School - Tennis Courts |
| TUE 5/14 | 3:15 PM | League | Stonington | Waterford | Stonington High School - SHS Tennis Courts |
| TUE 5/14 | 3:30 PM | Postseason | Seymour | Ansonia | Seymour High School - Tennis |
| TUE 5/14 | 3:45 PM | League | Branford | Cheshire | Branford High School - Tennis Courts |
| TUE 5/14 | 3:45 PM | League | East Haven | Sheehan | East Haven High School - Tennis Court |
| TUE 5/14 | 3:45 PM | League | Prince Tech | Platt Tech | Elizabeth Park - Elizabeth Park Courts 1,2,3,4,5,6 |
| TUE 5/14 | 3:45 PM | League | Fitch | Old Lyme | Fitch High School - Main Tennis Courts |
| TUE 5/14 | 3:45 PM | League | Granby Memorial | Canton | Granby Memorial High School - Tennis Courts |
| TUE 5/14 | 3:45 PM | League | Lewis Mills | Platt | Lewis Mills High School - Tennis Courts |
| TUE 5/14 | 3:45 PM | League | Morgan | Haddam-Killingworth | Morgan School - Tennis Courts |
| TUE 5/14 | 3:45 PM | League | Norwich Tech | Abbott Tech | Norwich Technical High School - NTHS Outdoor Athletic Complex |
| TUE 5/14 | 3:45 PM | League | Plainville | Bristol Eastern | Plainville High School - PHS Tennis Courts |
| TUE 5/14 | 3:45 PM | League | Rockville | Suffield | Rockville High School - RHS Tennis Courts |
| TUE 5/14 | 3:45 PM | League | St. Bernard | Montville | St. Bernard School - Tennis Courts |
| TUE 5/14 | 3:45 PM | League | Northwest Catholic | Middletown | University of Saint Joseph - Tennis Courts |
| TUE 5/14 | 3:45 PM | League | Wilcox Tech | Grasso Tech | Wilcox Tech - Tennis Courts |
| TUE 5/14 | 3:45 PM | Non-League | Bolton | BulkeleyHMTCA/Weaver | Bolton High School - BHS Tennis Courts |
| TUE 5/14 | 3:45 PM | Non-League | Portland | East Hampton | Portland High School - Tennis Courts |
| TUE 5/14 | 3:45 PM | Non-League | Cromwell | Coginchaug | Watrous park - Watrous park |
| TUE 5/14 | 3:45 PM | Non-League | Windsor Locks | Rocky Hill | Windsor Locks High School - Tennis Court |
| TUE 5/14 | 3:45 PM | Postseason | Watertown | Holy Cross | Crestbrook Park - Crestbrook Park Tennis Courts |
| TUE 5/14 | 4:00 PM | League | St. Paul Catholic | Torrington | Page Park - Tennis Courts |
| TUE 5/14 | 4:30 PM | League | Hall | Simsbury | Hall High School - Tennis Courts |
| TUE 5/14 | 5:30 PM | League | Rockville | Suffield | Rockville High School - RHS Tennis Courts |
| TUE 5/14 | 6:15 PM | League | Woodstock Academy | Ledyard | Pomfret School - Field House |
| WED 5/15 | 3:45 PM | League | Northwest Catholic | Glastonbury | Glastonbury Tennis Club - Tennis Courts |
| WED 5/15 | 3:45 PM | Non-League | Nonnewaug | Guilford | Nonnewaug High School - Tennis Courts |
| WED 5/15 | 4:00 PM | League | Newington | Bloomfield | Newington High School - Tennis Courts |
| WED 5/15 | 5:00 PM | Postseason | New Canaan | Darien | New Canaan HS - NCRC |
| WED 5/15 | Postponed | League | Lyman Memorial | New London | Lyman Memorial High School - Tennis Courts |
| WED 5/15 | Postponed | League | South Windsor | Tolland | South Windsor High School - Wapping Tennis Courts |
| THU 5/16 | 2:30 PM | League | North Haven | Sacred Heart Academy | North Haven Health & Racquet - North Haven Health & Racquet |
| THU 5/16 | 2:45 PM | Postseason | St. Paul Catholic | Naugatuck | Page Park - Tennis Courts |
| THU 5/16 | 3:45 PM | League | Housatonic Regional | Thomaston | Town Field - Town Tennis Courts |
| THU 5/16 | 4:15 PM | Non-League | Glastonbury | Amity | East Hartford Racquet Club - East Hartford Racquet Club |
| THU 5/16 | 5:00 PM | Non-League | Nonnewaug | Watertown | Nonnewaug High School - Middlebury Raquet Club |
| THU 5/16 | Postponed | League | Ellington | East Hartford | Ellington High School - Tennis Courts |
| THU 5/16 | Postponed | League | South Windsor | East Catholic | South Windsor High School - Wapping Tennis Courts |
| FRI 5/17 | 2:30 PM | League | North Branford | East Hampton | North Branford High School - NBHS Tennis Courts |
| FRI 5/17 | 3:30 PM | League | Killingly | Woodstock Academy | Killingly High School - Tennis Courts |
| FRI 5/17 | 3:30 PM | League | Old Saybrook | Coginchaug | Old Saybrook High School - Old Saybrook Tennis Courts |
| FRI 5/17 | 3:30 PM | League | Avon | Farmington | Sycamore Park - Sycamore Park |
| FRI 5/17 | 3:30 PM | League | West Haven | Hamden | West Haven High School - West Haven Tennis Courts |
| FRI 5/17 | 3:30 PM | Postseason | Wolcott | Woodland | Wolcott High School - WHS Tennis Courts |
| FRI 5/17 | 3:45 PM | League | Berlin | Plainville | Berlin High School - Tennis Courts |
| FRI 5/17 | 3:45 PM | League | Bolton | Coventry | Bolton High School - BHS Tennis Courts |
| FRI 5/17 | 3:45 PM | League | Bloomfield | Windsor | Carmen Arace - Tennis Courts |
| FRI 5/17 | 3:45 PM | League | Lyman Hall | East Haven | Doolittle Park - Doolittle Tennis Courts |
| FRI 5/17 | 3:45 PM | League | East Hartford | Manchester | East Hartford High School - Tennis Courts |
| FRI 5/17 | 3:45 PM | League | East Lyme | Old Lyme | East Lyme High School - Tennis Courts |
| FRI 5/17 | 3:45 PM | League | Prince Tech | Wilcox Tech | Elizabeth Park - Elizabeth Park Courts 1,2,3,4,5,6 |
| FRI 5/17 | 3:45 PM | League | Glastonbury | Simsbury | Glastonbury High School - Tennis Courts |
| FRI 5/17 | 3:45 PM | League | Maloney | Platt | Maloney High School - Tennis Courts |
| FRI 5/17 | 3:45 PM | League | New Britain | Southington | New Britain High School - tennis courts |
| FRI 5/17 | 3:45 PM | League | New London | Norwich Tech | New London High School - NLHS Tennis Courts |
| FRI 5/17 | 3:45 PM | League | Norwich Tech | Platt Tech | Norwich Technical High School - NTHS Outdoor Athletic Complex |
| FRI 5/17 | 3:45 PM | League | Norwich Free Academy | Montville | Rec Fields - Armstrong Tennis Courts |
| FRI 5/17 | 3:45 PM | Non-League | Sheehan | Portland | Sheehan High School - Sheehan HS Tennis Courts |
| FRI 5/17 | 3:45 PM | Non-League | Mercy | Ellington | Wesleyan University - Tennis Courts |
| FRI 5/17 | 4:00 PM | League | Newington | Wethersfield | Newington High School - Tennis Courts |
| FRI 5/17 | 5:00 PM | League | Waterford | Fitch | Waterford High School - Tennis Courts - WHS |
| FRI 5/17 | 5:30 PM | League | RHAM | Enfield | RHAM High School - Tennis Courts |
| SAT 5/18 | 10:00 AM | League | Fitch | Killingly | Fitch High School - Main Tennis Courts |
| SAT 5/18 | 11:00 AM | Postseason | Amity | Daniel Hand | Amity Regional High School - Tennis Courts |
| SAT 5/18 | 11:00 AM | Postseason | Watertown | Wolcott | Crestbrook Park - Crestbrook Park Tennis Courts |
| SAT 5/18 | 11:00 AM | Postseason | Greenwich | Fairfield Ludlowe | Greenwich High School - Tennis Courts |
| SAT 5/18 | 2:00 PM | Postseason | Cheshire | Mercy | Cheshire High School - Tennis Courts |
| SUN 5/19 | 1:00 PM | Non-League | Daniel Hand | Stonington | Polson Middle School, Madison - Polson Tennis Courts/DHHS Campus |
| SUN 5/19 | 12:00 PM | League | Fitch | East Lyme | Fitch High School - Main Tennis Courts |
| SUN 5/19 | 3:00 PM | Postseason | North Haven | Lauralton Hall | North Haven Athletic Complex - Tennis Courts |
| SUN 5/19 | 5:00 PM | League | Guilford | Hamden | Guilford High School - GHS Tennis Courts |
| MON 5/20 | 2:30 PM | League | Greenwich | | TBA - TBA |
| MON 5/20 | 2:45 PM | League | Coventry | East Granby | Coventry High School - tennis courts |
| MON 5/20 | 3:00 PM | Postseason | Stonington | St. Bernard, Fitch, Windham / Windham Tech, Norwich Free Academy, Woodstock Academy, Montville, Waterford, Ledyard, Killingly, East Lyme, Lyman Memorial | Stonington High School - SHS Tennis Courts |
| MON 5/20 | 3:30 PM | Non-League | Suffield | Simsbury | Suffield High School - Tennis Courts |
| MON 5/20 | 3:45 PM | League | Bristol Central | Bristol Eastern | Bristol Central High School - Tennis Courts |
| MON 5/20 | 3:45 PM | League | Bloomfield | Northwest Catholic | Carmen Arace - Tennis Courts |
| MON 5/20 | 3:45 PM | League | Career Magnet | Foran | Edgewood Park - Tennis Courts |
| MON 5/20 | 3:45 PM | League | Granby Memorial | Bolton | Granby Memorial High School - Tennis Courts |
| MON 5/20 | 3:45 PM | League | Middletown | Maloney | Middletown Tennis Courts - Beman Tennis Courts |
| MON 5/20 | 3:45 PM | League | RHAM | Wethersfield | RHAM High School - Tennis Courts |
| MON 5/20 | 3:45 PM | League | Rocky Hill | New Britain | Rocky Hill High School - tennis courts |
| MON 5/20 | 3:45 PM | League | Avon | Hall | Sycamore Park - Sycamore Park |
| MON 5/20 | 3:45 PM | League | Tolland | E.O. Smith | Tolland High School - Tennis Courts |
| MON 5/20 | 3:45 PM | League | Windsor | Platt | Windsor High School - Tennis Courts |
| MON 5/20 | 3:45 PM | Non-League | Rockville | Manchester | Rockville High School - RHS Tennis Courts |
| MON 5/20 | 3:45 PM | Postseason | Amity | Cheshire | Amity Regional High School - Tennis Courts |
| MON 5/20 | 4:00 PM | League | Ellington | East Catholic | Ellington High School - Tennis Courts |
| MON 5/20 | 8:15 AM | Postseason | Housatonic Regional | Shepaug Valley, Nonnewaug, Gilbert, Wamogo, Litchfield, Northwestern, Thomaston | Nonnewaug High School - Tennis Courts |
| MON 5/20 | 9:00 AM | Postseason | Grasso Tech | Wilcox Tech, Abbott Tech, Norwich Tech, Platt Tech, Prince Tech | Wesleyan - Middletown Tennis Courts |
| MON 5/20 | Canceled | League | East Hartford | Windsor Locks | East Hartford High School - Tennis Courts |
| TUE 5/21 | 12:01 AM | League | East Catholic | E.O. Smith | Wickham Park - Wickham Park |
| TUE 5/21 | 2:30 PM | League | Farmington | Hall | Irving Robbins Middle School - Tennis Courts |
| TUE 5/21 | 3:00 PM | Postseason | Stonington | Montville, Norwich Free Academy, Windham / Windham Tech, Woodstock Academy, Waterford, St. Bernard, Fitch, East Lyme, Lyman Memorial, Killingly, Ledyard | Stonington High School - SHS Tennis Courts |
| TUE 5/21 | 3:30 PM | League | Avon | Conard | Sycamore Park - Sycamore Park |
| TUE 5/21 | 3:30 PM | League | Windsor Locks | East Granby | Windsor Locks High School - Tennis Court |
| TUE 5/21 | 3:30 PM | Non-League | Pomperaug | Litchfield | Edgewood Bath and Tennis Club - Edgewood Bath and Tennis Club |
| TUE 5/21 | 3:45 PM | League | Berlin | Bristol Central | Berlin High School - Tennis Courts |
| TUE 5/21 | 3:45 PM | League | Granby Memorial | Rockville | Granby Memorial High School - Tennis Courts |
| TUE 5/21 | 3:45 PM | League | Killingly | Norwich Free Academy | Killingly High School - Tennis Courts |
| TUE 5/21 | 3:45 PM | League | Middletown | Lewis Mills | Middletown Tennis Courts - Beman Tennis Courts |
| TUE 5/21 | 3:45 PM | League | Plainville | Tolland | Plainville High School - PHS Tennis Courts |
| TUE 5/21 | 3:45 PM | League | RHAM | East Hartford | RHAM High School - Tennis Courts |
| TUE 5/21 | 3:45 PM | League | Windsor | Wethersfield | Windsor High School - Tennis Courts |
| TUE 5/21 | 3:45 PM | Non-League | Lyman Hall | North Branford | Doolittle Park - Doolittle Tennis Courts |
| TUE 5/21 | 3:45 PM | Non-League | New Britain | Wilcox Tech | New Britain High School - tennis courts |
| TUE 5/21 | 4:00 PM | League | Canton | Northwest Catholic | Mills Pond Park - Canton - Mills Pond |
| TUE 5/21 | 4:00 PM | League | Suffield | Enfield | Suffield High School - Tennis Courts |
| TUE 5/21 | 4:00 PM | Non-League | Newington | Ellington | Newington High School - Tennis Courts |
| WED 5/22 | 1:00 PM | Postseason | Housatonic Regional | Litchfield, Northwestern, Thomaston, Wamogo, Nonnewaug, Shepaug Valley | Nonnewaug High School - Tennis Courts |
| WED 5/22 | 2:00 PM | League | Conard | Hall | Conard High School - Tennis Courts |
| WED 5/22 | 3:00 PM | Postseason | Stonington | Montville, Waterford, Norwich Free Academy, Woodstock Academy, Windham / Windham Tech, St. Bernard, Fitch, Lyman Memorial, East Lyme, Ledyard, Killingly | Stonington High School - SHS Tennis Courts |
| WED 5/22 | 3:30 PM | Non-League | Platt | Wilcox Tech | Platt High School - Tennis Court |
| WED 5/22 | 3:45 PM | League | Bloomfield | Tolland | Carmen Arace - Tennis Courts |
| WED 5/22 | 3:45 PM | League | East Hartford | Rocky Hill | East Hartford High School - Tennis Courts |
| WED 5/22 | 3:45 PM | League | Enfield | Manchester | Enfield High School - EHS TENNIS COURTS |
| WED 5/22 | 3:45 PM | League | Southington | Simsbury | Southington High School - Tennis Courts |
| WED 5/22 | 4:00 PM | Non-League | Morgan | Westbrook | Morgan School - Tennis Courts |
| WED 5/22 | 4:00 PM | Non-League | St. Joseph | Joel Barlow | St. Joseph High School - Tennis Courts |
| WED 5/22 | 9:00 AM | League | Rockville | Canton, Ellington, Coventry, Bolton, Granby Memorial, Suffield, East Granby, Windsor Locks | Rockville High School - RHS Tennis Courts |
| FRI 5/24 | 12:01 AM | Postseason | Ridgefield | | Ridgefield High School - RHS Tennis Courts |
| SAT 5/25 | 12:01 AM | Postseason | Ridgefield | | Ridgefield High School - RHS Tennis Courts |
| TUE 5/28 | 12:01 AM | Postseason | Ridgefield | | Ridgefield High School - RHS Tennis Courts |
| WED 5/29 | 12:01 AM | Postseason | Ridgefield | | Ridgefield High School - RHS Tennis Courts |
| THU 5/30 | 12:01 AM | Postseason | Ridgefield | | Ridgefield High School - RHS Tennis Courts |
| SUN 6/2 | 12:01 AM | Postseason | Ridgefield | | Ridgefield High School - RHS Tennis Courts |