| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 8/21 | 3:00 PM | Varsity | League | Normal | Away | Wethersfield | | | | Wethersfield Country Club - Wethersfield Country Club | |
| Northwest Catholic | | |
| WED 9/4 | 3:00 PM | Varsity | Non-League | Normal | Away | Newington | | | | Indian Hill Country Club - Indian Hill Country Club | |
| THU 9/5 | 2:50 PM | Varsity | Non-League | Normal | Away | Fairfield Ludlowe | | | | Smith Richardson Golf Course - Smith Richardson Golf Course | |
| MON 9/9 | 9:00 AM | Varsity | Non-League | Normal | Away | Avon | | | | Timberlin Golf Course - Timberlin Golf Course | |
| Berlin | | |
| Conard | | |
| St. Joseph | | |
| Farmington | | |
| Glastonbury | | |
| Pomperaug | | |
| THU 9/12 | 3:00 PM | Varsity | Non-League | Normal | Away | Fairfield Warde | | | | Smith Richardson Golf Course - Smith Richardson Golf Course | |
| WED 9/25 | 3:00 PM | Varsity | Non-League | Normal | Away | Glastonbury | | | | Glastonbury Hills Country Club - Glastonbury Hills Country Club | |
| THU 9/26 | 3:00 PM | Varsity | League | Normal | Away | Immaculate | | | | [CIAC] Orange Hill GC - [CIAC] Orange Hill GC | 12:00 PM |
| Pomperaug | | |
| Weston | | |
| Brookfield | | |
| Brookfield | | |
| New Fairfield | | |
| Trumbull | | |
| Wamogo | | |
| Rocky Hill | | |
| Danbury | | |
| Joel Barlow | | |
| Shepaug Valley | | |
| | |
| TUE 10/1 | 3:00 PM | Varsity | Non-League | Normal | Away | Fairfield Ludlowe | | | | CC of Fairfield - CC of Fairfield | |
| Fairfield Warde | | |