| Date | Time | Type | Home School | Away School | Site |
| TUE 8/22 | 2:50 PM | League | Fairfield Ludlowe | Ridgefield | Smith Richardson Golf Course - Smith Richardson Golf Course |
| THU 8/24 | 3:00 PM | League | Danbury | New Canaan | Richter Park Golf Course - Richter Park Golf Course |
| THU 8/24 | 3:00 PM | League | Hall | Avon | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| THU 8/24 | 3:15 PM | League | St. Joseph | Brien McMahon | Tashua Knolls Golf Course - Tashua Glen |
| THU 8/24 | 3:30 PM | League | Darien | Wilton | Woodway Country Club - Woodway Country Club |
| THU 8/24 | Canceled | League | Ridgefield | Trumbull | Silver Spring Golf Course - Silver Spring Golf Course |
| MON 8/28 | 3:00 PM | League | Darien | Fairfield Warde | Wee Burn CC - Wee Burn CC |
| TUE 8/29 | 3:00 PM | League | Glastonbury | Wethersfield | Minnechaug Golf Course - Minnechaug Golf Course |
| TUE 8/29 | 3:00 PM | League | Danbury | Wilton | Richter Park Golf Course - Richter Park Golf Course |
| TUE 8/29 | 3:15 PM | League | Trumbull | Fairfield Ludlowe | Tashua Knolls Golf Course - Tashua Glen |
| WED 8/30 | 3:15 PM | League | St. Joseph | Ridgefield | Tashua Knolls Golf Course - Tashua Glen |
| WED 8/30 | 3:30 PM | League | Brien McMahon | Fairfield Warde | Oak Hills Golf Course - Oak Hills Golf Course |
| THU 8/31 | 3:00 PM | League | Fairfield Prep | Fairfield Ludlowe | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| THU 8/31 | 3:00 PM | League | Staples | Ridgefield | Longshore Golf Course - Longshore Golf Course |
| THU 8/31 | 3:00 PM | League | Hall | Southington | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| THU 8/31 | 3:00 PM | League | Berlin | Glastonbury | Timberlin Golf Course - Timberlin Golf Course |
| THU 8/31 | 3:15 PM | League | New Canaan | Darien | New Canaan HS - CCNC |
| THU 8/31 | 3:30 PM | League | Brien McMahon | New Canaan | Oak Hills Golf Course - Oak Hills Golf Course |
| TUE 9/5 | 2:50 PM | League | Fairfield Ludlowe | New Canaan | Smith Richardson Golf Course - Smith Richardson Golf Course |
| TUE 9/5 | 3:00 PM | League | Conard | Lewis Mills | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 9/5 | 3:00 PM | League | Fairfield Warde | Trumbull | Smith Richardson Golf Course - Smith Richardson Golf Course |
| WED 9/6 | 3:00 PM | League | Staples | Fairfield Prep | Longshore Golf Course - Longshore Golf Course |
| WED 9/6 | 3:30 PM | League | Brien McMahon | Wilton | Brien McMahon High School - Oak Hills Golf Course |
| WED 9/6 | Postponed | League | Wethersfield | Avon | Goodwin Park Golf Course - Goodwin Park Golf Course |
| WED 9/6 | Postponed | League | Trumbull | St. Joseph | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| WED 9/6 | Postponed | League | Berlin | Newington | Timberlin Golf Course - Timberlin Golf Course |
| THU 9/7 | 3:15 PM | League | Trumbull | Staples | Tashua Knolls Golf Course - Tashua Glen |
| THU 9/7 | 3:30 PM | League | Brien McMahon | Darien | Brien McMahon High School - Oak Hills Golf Course |
| THU 9/7 | 3:30 PM | League | Greenwich | Fairfield Prep | Griffith E Harris Golf Course - Griffith E Harris Golf Course |
| MON 9/11 | Postponed | Non-League | Berlin | Fairfield Prep | Timberlin Golf Course - Timberlin Golf Course |
| TUE 9/12 | 3:00 PM | League | Fairfield Prep | Darien | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| TUE 9/12 | 3:00 PM | League | Conard | Southington | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 9/12 | 3:00 PM | Non-League | Glastonbury | Newington | Minnechaug Golf Course - Minnechaug Golf Course |
| TUE 9/12 | 3:10 PM | League | Greenwich | Fairfield Ludlowe | Griffith E Harris Golf Course - Griffith E Harris Golf Course |
| WED 9/13 | 2:50 PM | League | Fairfield Ludlowe | Fairfield Warde | Smith Richardson Golf Course - Smith Richardson Golf Course |
| WED 9/13 | 3:15 PM | League | St. Joseph | New Canaan | Tashua Knolls Golf Course - Tashua Glen |
| WED 9/13 | 3:30 PM | League | Greenwich | New Canaan | Griffith E Harris Golf Course - Griffith E Harris Golf Course |
| WED 9/13 | Postponed | League | Avon | Wethersfield | Blue Fox Run Golf Course - Blue Fox Run Golf Course |
| THU 9/14 | 2:50 PM | League | Fairfield Ludlowe | Darien | Smith Richardson Golf Course - Smith Richardson Golf Course |
| THU 9/14 | 3:00 PM | League | Fairfield Warde | Westhill | Brooklawn Country Club - Brooklawn Country Club |
| THU 9/14 | 3:00 PM | League | Wethersfield | Glastonbury | Goodwin Park Golf Course - Goodwin Park Golf Course |
| THU 9/14 | 3:00 PM | League | Conard | Hall | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| THU 9/14 | 3:15 PM | League | Trumbull | St. Joseph | Tashua Knolls Golf Course - Tashua Glen |
| MON 9/18 | Postponed | League | New Canaan | Wilton | CCNC - CCNC |
| MON 9/18 | Postponed | Non-League | Glastonbury | Fairfield Prep | Minnechaug Golf Course - Minnechaug Golf Course |
| TUE 9/19 | 3:00 PM | League | Danbury | Fairfield Ludlowe | Richter Park Golf Course - Richter Park Golf Course |
| TUE 9/19 | 3:00 PM | League | Ridgefield | Darien | Silver Spring Golf Course - Silver Spring Golf Course |
| TUE 9/19 | 3:30 PM | League | Wilton | Fairfield Warde | Rolling Hills Country Club - Rolling Hills Country Club |
| WED 9/20 | 3:00 PM | League | Wethersfield | Berlin | Goodwin Park Golf Course - Goodwin Park Golf Course |
| WED 9/20 | 3:15 PM | League | Staples | New Canaan | Longshore Golf Course - Longshore Golf Course |
| WED 9/20 | 3:15 PM | League | Fairfield Warde | Fairfield Prep | Patterson Club - Patterson Club |
| WED 9/20 | 3:15 PM | League | St. Joseph | Fairfield Ludlowe | Tashua Knolls Golf Course - Tashua Glen |
| WED 9/20 | 3:30 PM | League | Greenwich | Darien | Greenwich Country Club - Greenwich Country Club |
| THU 9/21 | 3:00 PM | League | Newington | Berlin | Indian Hill Country Club - Indian Hill Country Club |
| THU 9/21 | 3:00 PM | League | Danbury | Darien | Richter Park Golf Course - Richter Park Golf Course |
| THU 9/21 | 3:00 PM | League | Hall | Simsbury | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| THU 9/21 | 3:00 PM | League | Ridgefield | Wilton | Silver Spring Golf Course - Silver Spring Golf Course |
| THU 9/21 | 3:00 PM | League | Simsbury | Glastonbury | Simsbury High School - Simsbury Farms CC |
| THU 9/21 | 3:00 PM | League | Fairfield Warde | Staples | Smith Richardson Golf Course - Smith Richardson Golf Course |
| FRI 9/22 | 3:00 PM | League | Conard | Simsbury | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 9/26 | 2:50 PM | League | Fairfield Ludlowe | Brien McMahon | Smith Richardson Golf Course - Smith Richardson Golf Course |
| TUE 9/26 | 3:00 PM | League | Darien | New Canaan | Country Club of Darien - Country Club of Darien |
| TUE 9/26 | 3:00 PM | League | Fairfield Prep | Greenwich | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| TUE 9/26 | 3:00 PM | League | Danbury | Ridgefield | Richter Park Golf Course - Richter Park Golf Course |
| TUE 9/26 | 3:00 PM | League | Southington | Berlin | Southington High School - Southington Country Club |
| TUE 9/26 | 3:15 PM | League | St. Joseph | Darien | Tashua Knolls Golf Course - Tashua Glen |
| WED 9/27 | 2:50 PM | League | Fairfield Ludlowe | Wilton | Smith Richardson Golf Course - Smith Richardson Golf Course |
| WED 9/27 | 3:00 PM | League | Glastonbury | Wethersfield | Minnechaug Golf Course - Minnechaug Golf Course |
| WED 9/27 | 3:15 PM | League | Staples | Darien | Longshore Golf Course - Longshore Golf Course |
| WED 9/27 | 3:15 PM | League | St. Joseph | Danbury | Tashua Knolls Golf Course - Tashua Glen |
| THU 9/28 | 3:00 PM | League | New Canaan | Fairfield Ludlowe | CCNC - CCNC |
| THU 9/28 | 3:00 PM | League | Newtown | Pomperaug | Newtown Country Club - Newtown Country Club |
| THU 9/28 | 3:00 PM | League | Fairfield Warde | St. Joseph | Patterson Club - Patterson Club |
| THU 9/28 | 3:00 PM | League | Conard | Northwest Catholic | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| THU 9/28 | 3:30 PM | League | Wilton | Staples | Rolling Hills Country Club - Rolling Hills Country Club |
| MON 10/2 | 3:00 PM | League | Hall | Conard, Newington, Glastonbury | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| MON 10/2 | 3:15 PM | League | Wilton | Darien | Rolling Hills Country Club - Rolling Hills Country Club |
| MON 10/2 | 3:30 PM | League | New Canaan | Greenwich | CCNC - CCNC |
| TUE 10/3 | 3:00 PM | League | Darien | Greenwich | Country Club of Darien - Country Club of Darien |
| TUE 10/3 | 3:00 PM | League | Wethersfield | Newington | Goodwin Park Golf Course - Goodwin Park Golf Course |
| TUE 10/3 | 3:00 PM | League | Hall | Farmington | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 10/3 | 3:15 PM | League | Trumbull | Danbury | Tashua Knolls Golf Course - Tashua Glen |
| TUE 10/3 | 3:15 PM | Non-League | New Canaan | Fairfield Prep | CCNC - CCNC |
| WED 10/4 | 3:00 PM | League | Berlin | Wethersfield | Timberlin Golf Course - Timberlin Golf Course |
| WED 10/4 | 3:15 PM | League | St. Joseph | Staples | Tashua Knolls Golf Course - Tashua Glen |
| WED 10/4 | 3:30 PM | League | New Canaan | Fairfield Warde | CCNC - CCNC |
| WED 10/4 | 3:30 PM | League | Wilton | Trumbull | Rolling Hills Country Club - Rolling Hills Country Club |
| WED 10/4 | Postponed | Non-League | Darien | Fairfield Prep | Wee Burn CC - Wee Burn CC |
| THU 10/5 | 3:00 PM | League | Newington | Wethersfield | Indian Hill Country Club - Indian Hill Country Club |
| THU 10/5 | 3:00 PM | League | Glastonbury | Berlin | Minnechaug Golf Course - Minnechaug Golf Course |
| THU 10/5 | 3:00 PM | League | Ridgefield | Fairfield Prep | Ridgefield Golf Course - Ridgefield Golf Course |
| MON 10/9 | 3:15 PM | League | Staples | Fairfield Ludlowe | Longshore Golf Course - Longshore Golf Course |
| MON 10/9 | 3:15 PM | League | Wilton | New Canaan | Rolling Hills Country Club - Rolling Hills Country Club |
| TUE 10/10 | 3:00 PM | League | Avon | Simsbury | Blue Fox Run Golf Course - Blue Fox Run Golf Course |
| TUE 10/10 | 3:00 PM | League | Hall | Northwest Catholic | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 10/10 | 3:00 PM | League | Fairfield Ludlowe | Fairfield Prep, Fairfield Warde | Smith Richardson Golf Course - Smith Richardson Golf Course |
| TUE 10/10 | 3:15 PM | League | New Canaan | Staples | CCNC - CCNC |
| TUE 10/10 | 3:30 PM | League | Wilton | Greenwich | Rolling Hills Country Club - Rolling Hills Country Club |
| TUE 10/10 | Canceled | League | Newington | Glastonbury | Indian Hill Country Club - Indian Hill Country Club |
| WED 10/11 | 3:15 PM | League | Trumbull | Fairfield Prep | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| WED 10/11 | 3:30 PM | League | New Canaan | Darien | CCNC - CCNC |
| THU 10/12 | 3:00 PM | League | Fairfield Prep | Berlin | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| THU 10/12 | 3:00 PM | League | Wethersfield | Glastonbury | Goodwin Park Golf Course - Goodwin Park Golf Course |
| THU 10/12 | 3:00 PM | League | Hall | Conard | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| THU 10/12 | 3:00 PM | Non-League | Ridgefield | Immaculate | Silver Spring Golf Course - Silver Spring Golf Course |
| THU 10/12 | 3:10 PM | League | Darien | Greenwich | Woodway Country Club - Woodway Country Club |
| THU 10/12 | 3:15 PM | League | St. Joseph | Wilton | Tashua Knolls Golf Course - Tashua Glen |
| THU 10/12 | 3:30 PM | League | New Canaan | Trumbull | CCNC - CCNC |
| MON 10/16 | 3:30 PM | League | Brien McMahon | Darien | Brien McMahon High School - Oak Hills Golf Course |
| TUE 10/17 | 3:00 PM | League | Conard | Farmington | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 10/17 | 3:45 PM | League | Fairfield Prep | Glastonbury | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| WED 10/18 | 3:00 PM | League | Darien | Staples | Woodway Country Club - Woodway Country Club |