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