| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 8/31 | 3:00 PM | Varsity | Non-League | Normal | Home | Joel Barlow | | | | Whitney Farms Golf Course - Whitney Farms Golf Course | |
| TUE 9/5 | 3:00 PM | Varsity | Non-League | Normal | Away | New Milford | | | | Candlewood Valley Country Club - Candlewood Valley Country Club | 1:30 PM - 1 Bus |
| WED 9/6 | 3:00 PM | Varsity | League | Normal | Home | Brookfield | | | | Whitney Farms Golf Course - Whitney Farms Golf Course | |
| TUE 9/12 | 3:00 PM | Varsity | Non-League | Normal | Home | Brookfield | | | | Whitney Farms Golf Course - Whitney Farms Golf Course | |
| WED 9/13 | Postponed | Varsity | League | Postponed | Away | Pomperaug | | | | Pomperaug High School - Highfield Country Club | 1:30 PM - 1 Bus |
| WED 9/20 | 3:30 PM | Varsity | League | Normal | Away | Newtown | | | | Rock Ridge Country Club - Rock Ridge Country Club | 2:30 PM - 1 Bus |
| THU 9/21 | 3:00 PM | Varsity | League | Normal | Home | Immaculate | | | | Whitney Farms Golf Course - Whitney Farms Golf Course | |
| TUE 9/26 | 3:00 PM | Varsity | Non-League | Normal | Home | Bunnell | | | | Whitney Farms Golf Course - Whitney Farms Golf Course | |
| WED 9/27 | 3:00 PM | Varsity | League | Normal | Away | Notre Dame-Fairfield | | | | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course | 1:45 PM - 1 Bus |
| THU 9/28 | 2:30 PM | Varsity | League | Normal | Away | Brien McMahon | | | | [CIAC] SMSA - [CIAC] SMSA | |
| Fairfield Prep | | |
| Gilbert | | |
| Rocky Hill | | |
| | |
| TUE 10/3 | 2:00 PM | Varsity | League | Normal | Home | Stratford | | | | Whitney Farms Golf Course - Whitney Farms Golf Course | |
| WED 10/4 | 3:00 PM | Varsity | League | Normal | Away | Weston | | | | Weston High School - Aspetuck Country Club | 2:10 PM - 1 Bus |
| THU 10/5 | 3:00 PM | Varsity | League | Normal | Home | New Milford | | | | Whitney Farms Golf Course - Whitney Farms Golf Course | |
| MON 10/9 | Postponed | Varsity | League | Postponed | Away | Immaculate | | | | Immaculate High School - Ridgewood CC | 1:30 PM - 1 Bus |
| TUE 10/10 | 3:00 PM | Varsity | League | Normal | Away | Bethel | | | | Bethel High School - Connecticut Country Club | 1:45 PM - 1 Bus |
| WED 10/11 | 3:00 PM | Varsity | League | Normal | Away | Bethel | | | | Pomperaug High School - Highfield Country Club | |
| Pomperaug | | |
| WED 10/18 | 8:30 AM | Varsity | Postseason | Normal | Away | Bethel | | | | TBA - TBA | 7:00 AM |
| Brookfield | | |
| Bunnell | | |
| Immaculate | | |
| Joel Barlow | | |
| New Fairfield | | |
| New Milford | | |
| Newtown | | |
| Notre Dame-Fairfield | | |
| Pomperaug | | |
| Stratford | | |
| Weston | | |