| Date | Time | Type | Home School | Away School | Site |
| SAT 8/16 | 3:00 PM | League | Wethersfield | Glastonbury | Goodwin Park Golf Course - Goodwin Park Golf Course |
| TUE 8/19 | Postponed | League | Fairfield Prep | Darien | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| WED 8/20 | 3:00 PM | League | Brien McMahon | Wilton | Brien McMahon High School - Oak Hills Golf Course |
| WED 8/20 | 3:15 PM | League | Staples | Danbury | Longshore Golf Course - Longshore Golf Course |
| THU 8/21 | 3:00 PM | League | Hall | Avon | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 8/26 | 3:00 PM | League | Staples | Darien | Longshore Golf Course - Longshore Golf Course |
| TUE 8/26 | 3:00 PM | League | Conard | Southington | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 8/26 | 3:00 PM | League | Fairfield Ludlowe | Brien McMahon | Smith Richardson Golf Course - Smith Richardson Golf Course |
| WED 8/27 | 3:30 PM | League | New Canaan | Wilton | New Canaan HS - CCNC |
| THU 8/28 | 3:00 PM | League | Newington | Wethersfield | Indian Hill Country Club - Indian Hill Country Club |
| THU 8/28 | 3:00 PM | League | Hall | Southington | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| THU 8/28 | 3:00 PM | League | Fairfield Warde | St. Joseph | Smith Richardson Golf Course - Smith Richardson Golf Course |
| THU 8/28 | 3:30 PM | League | New Canaan | Darien | New Canaan HS - CCNC |
| TUE 9/2 | 3:00 PM | League | Glastonbury | Wethersfield | Minnechaug Golf Course - Minnechaug Golf Course |
| TUE 9/2 | 3:00 PM | League | Conard | Farmington | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 9/2 | 3:00 PM | League | Darien | Wilton | Woodway Country Club - Woodway Country Club |
| TUE 9/2 | 3:15 PM | League | Staples | Brien McMahon | Longshore Golf Course - Longshore Golf Course |
| TUE 9/2 | 3:30 PM | League | New Canaan | Greenwich | New Canaan HS - CCNC |
| WED 9/3 | 3:00 PM | League | Brien McMahon | Fairfield Warde | Brien McMahon High School - Oak Hills Golf Course |
| WED 9/3 | 3:00 PM | League | Fairfield Ludlowe | Darien | Smith Richardson Golf Course - Smith Richardson Golf Course |
| WED 9/3 | 3:10 PM | League | St. Joseph | Wilton | Tashua Knolls Golf Course - Tashua Glen |
| THU 9/4 | 3:00 PM | League | Newington | Glastonbury | Indian Hill Country Club - Indian Hill Country Club |
| THU 9/4 | 3:00 PM | League | Conard | Hall | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| THU 9/4 | 3:00 PM | League | Fairfield Warde | Danbury | Smith Richardson Golf Course - Smith Richardson Golf Course |
| THU 9/4 | 3:00 PM | League | Farmington | Simsbury | Tunxis Country Club - Tunxis Country Club |
| THU 9/4 | 3:10 PM | League | St. Joseph | Ridgefield | Tashua Knolls Golf Course - Tashua Glen |
| THU 9/4 | 3:15 PM | League | Staples | Westhill | Longshore Golf Course - Longshore Golf Course |
| MON 9/8 | 3:00 PM | League | Berlin | Glastonbury | Timberlin Golf Course - Timberlin Golf Course |
| TUE 9/9 | 3:00 PM | League | Conard | Lewis Mills | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 9/9 | 3:00 PM | League | Rocky Hill | Wethersfield | Rolling Greens - Rolling Greens |
| TUE 9/9 | 3:00 PM | League | Fairfield Ludlowe | Greenwich | Smith Richardson Golf Course - Smith Richardson Golf Course |
| TUE 9/9 | 3:00 PM | League | Farmington | Hall | Tunxis Country Club - Tunxis Country Club |
| WED 9/10 | 2:51 PM | League | Fairfield Warde | | Smith Richardson Golf Course - Smith Richardson Golf Course |
| WED 9/10 | 3:00 PM | League | Brien McMahon | Darien | Brien McMahon High School - Oak Hills Golf Course |
| WED 9/10 | 3:00 PM | League | Southington | Berlin | Southington High School - Southington Country Club |
| WED 9/10 | 3:30 PM | League | Staples | Ridgefield | Longshore Golf Course - Longshore Golf Course |
| WED 9/10 | 3:30 PM | League | New Canaan | Fairfield Prep | New Canaan HS - CCNC |
| THU 9/11 | 3:00 PM | League | Glastonbury | Rocky Hill | Minnechaug Golf Course - Minnechaug Golf Course |
| THU 9/11 | 3:00 PM | League | Ridgefield | Darien | Ridgefield Golf Course - Ridgefield Golf Course |
| THU 9/11 | 3:00 PM | League | Fairfield Warde | Staples | Smith Richardson Golf Course - Smith Richardson Golf Course |
| THU 9/11 | 3:00 PM | League | Farmington | Northwest Catholic | Tunxis Country Club - Tunxis Country Club |
| THU 9/11 | 3:10 PM | League | St. Joseph | Fairfield Ludlowe | Tashua Knolls Golf Course - Tashua Glen |
| THU 9/11 | 3:30 PM | League | New Canaan | Trumbull | New Canaan HS - CCNC |
| MON 9/15 | 3:00 PM | League | Darien | Greenwich | Wee Burn CC - Wee Burn CC |
| MON 9/15 | 3:15 PM | League | Staples | Ridgefield | Longshore Golf Course - Longshore Golf Course |
| TUE 9/16 | 3:00 PM | League | Wethersfield | Newington, Glastonbury | Goodwin Park Golf Course - Goodwin Park Golf Course |
| TUE 9/16 | 3:00 PM | League | Hall | Northwest Catholic | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 9/16 | 3:00 PM | League | Fairfield Ludlowe | Ridgefield | Smith Richardson Golf Course - Smith Richardson Golf Course |
| TUE 9/16 | 3:00 PM | League | Farmington | Lewis Mills | Tunxis Country Club - Tunxis Country Club |
| TUE 9/16 | 3:10 PM | League | St. Joseph | Darien | Tashua Knolls Golf Course - Tashua Glen |
| WED 9/17 | 3:00 PM | League | Brien McMahon | New Canaan | Brien McMahon High School - Oak Hills Golf Course |
| WED 9/17 | 3:00 PM | League | Rocky Hill | Berlin | Rolling Greens - Rolling Greens |
| WED 9/17 | 3:00 PM | League | Darien | Staples | Woodway Country Club - Woodway Country Club |
| THU 9/18 | 3:00 PM | League | Wethersfield | Rocky Hill | Goodwin Park Golf Course - Goodwin Park Golf Course |
| THU 9/18 | 3:00 PM | League | Fairfield Warde | Trumbull | Smith Richardson Golf Course - Smith Richardson Golf Course |
| THU 9/18 | 3:00 PM | Non-League | Ridgefield | Fairfield Prep | Ridgefield Golf Course - Ridgefield Golf Course |
| FRI 9/19 | 3:00 PM | League | Conard | Simsbury | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| MON 9/22 | 3:00 PM | League | Berlin | Newington | Timberlin Golf Course - Timberlin Golf Course |
| MON 9/22 | 3:00 PM | League | Darien | Staples | Wee Burn CC - Wee Burn CC |
| WED 9/24 | 3:00 PM | League | Brien McMahon | Ridgefield | Brien McMahon High School - Oak Hills Golf Course |
| WED 9/24 | 3:00 PM | League | Wethersfield | Avon | Goodwin Park Golf Course - Goodwin Park Golf Course |
| WED 9/24 | 3:00 PM | League | Newington | Conard | Indian Hill Country Club - Indian Hill Country Club |
| WED 9/24 | 3:00 PM | League | Glastonbury | Fairfield Prep, Berlin | Minnechaug Golf Course - Minnechaug Golf Course |
| WED 9/24 | 3:00 PM | League | Fairfield Ludlowe | Wilton | Smith Richardson Golf Course - Smith Richardson Golf Course |
| WED 9/24 | 3:20 PM | League | Darien | Greenwich | Woodway Country Club - Woodway Country Club |
| WED 9/24 | 3:30 PM | League | New Canaan | Fairfield Warde | New Canaan HS - CCNC |
| THU 9/25 | 3:00 PM | League | Newington | Wethersfield | Indian Hill Country Club - Indian Hill Country Club |
| MON 9/29 | 3:00 PM | League | Glastonbury | Avon | Minnechaug Golf Course - Minnechaug Golf Course |
| MON 9/29 | 3:00 PM | League | Hall | Simsbury | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| MON 9/29 | 3:00 PM | League | Darien | Trumbull | Wee Burn CC - Wee Burn CC |
| MON 9/29 | 3:15 PM | League | Staples | Fairfield Ludlowe | Longshore Golf Course - Longshore Golf Course |
| TUE 9/30 | 3:10 PM | League | St. Joseph | New Canaan | Tashua Knolls Golf Course - Tashua Glen |
| WED 10/1 | 3:00 PM | League | Darien | New Canaan | Country Club of Darien - Country Club of Darien |
| WED 10/1 | 3:00 PM | League | Wethersfield | Glastonbury | Goodwin Park Golf Course - Goodwin Park Golf Course |
| WED 10/1 | 3:00 PM | League | Conard | Northwest Catholic | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| WED 10/1 | 3:00 PM | League | Farmington | Avon | Tunxis Country Club - Tunxis Country Club |
| THU 10/2 | 3:00 PM | League | Northwest Catholic | Wethersfield | Wampanoag Country Club - Wampanoag Country Club |
| MON 10/6 | 3:00 PM | League | Glastonbury | Newington | Minnechaug Golf Course - Minnechaug Golf Course |
| MON 10/6 | 3:00 PM | League | Berlin | Southington | Timberlin Golf Course - Timberlin Golf Course |
| MON 10/6 | 3:00 PM | League | Farmington | Conard | Tunxis Country Club - Tunxis Country Club |
| MON 10/6 | 3:15 PM | League | Staples | St. Joseph | Longshore Golf Course - Longshore Golf Course |
| TUE 10/7 | 3:00 PM | League | Ridgefield | Trumbull | Ridgefield Golf Course - Ridgefield Golf Course |
| TUE 10/7 | 3:00 PM | League | Hall | Farmington | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 10/7 | 3:00 PM | League | Fairfield Warde | | Smith Richardson Golf Course - Smith Richardson Golf Course |
| TUE 10/7 | 3:10 PM | League | St. Joseph | Danbury | Tashua Knolls Golf Course - Tashua Glen |
| WED 10/8 | 3:00 PM | League | Fairfield Ludlowe | New Canaan | Smith Richardson Golf Course - Smith Richardson Golf Course |
| WED 10/8 | 3:00 PM | League | Berlin | Avon | Timberlin Golf Course - Timberlin Golf Course |
| WED 10/8 | 3:00 PM | League | Farmington | Southington | Tunxis Country Club - Tunxis Country Club |
| WED 10/8 | 3:10 PM | League | St. Joseph | Brien McMahon | Tashua Knolls Golf Course - Tashua Glen |
| WED 10/8 | 4:00 PM | Non-League | Darien | Fairfield Prep | Country Club of Darien - Country Club of Darien |
| WED 10/8 | Canceled | League | Simsbury | Glastonbury | Hop Meadow Country Club - Hop Meadow Country Club |
| WED 10/8 | Canceled | League | Berlin | Wethersfield, Rocky Hill | Timberlin Golf Course - Timberlin Golf Course |
| THU 10/9 | 3:00 PM | League | Glastonbury | Wethersfield | Minnechaug Golf Course - Minnechaug Golf Course |
| TUE 10/14 | 3:00 PM | League | Hall | Conard | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| WED 10/15 | 2:30 PM | League | Ridgefield | Wilton | Ridgefield Golf Course - Ridgefield Golf Course |
| WED 10/15 | 3:00 PM | League | Brien McMahon | Norwalk | Shorehaven Golf Club - Shorehaven Golf Club |
| WED 10/15 | 3:15 PM | League | Fairfield Prep | Fairfield Ludlowe, Fairfield Warde | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| THU 10/16 | Canceled | League | Glastonbury | Rocky Hill | Minnechaug Golf Course - Minnechaug Golf Course |