| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/6 | 3:15 PM | Varsity | League | Normal | Away | | | | | [CIAC] Middletown - [CIAC] Middletown | 1:25 PM - 1 Bus |
| WED 9/11 | 3:30 PM | Varsity | League | Normal | Away | Branford | Loss | 39-102 | | Branford Supply Pond - Branford Supply Pond | 2:15 PM - 1 Bus |
| Daniel Hand | Loss | 39-69 |
| Shelton | Loss | 39-27 |
| TUE 9/17 | 3:45 PM | Varsity | League | Normal | Home | Lyman Hall | | | | Hamden Middle School - Back Field | |
| North Haven | | |
| Guilford | | |
| SAT 9/21 | 9:00 AM | Varsity | League | Normal | Away | | | | | Winding Trails - Cross Country Course | 12:01 AM |
| SAT 9/28 | 9:00 AM | Varsity | League | Normal | Away | | | | | Wickham Park - Wickham Park | 12:01 AM |
| WED 10/2 | 4:30 PM | Varsity | League | Normal | Away | | | | | Guilford Fairgrounds - Guilford Fairgrounds | 2:00 PM |
| MON 10/7 | 3:45 PM | Varsity | League | Normal | Away | Hillhouse | | | | Fitzgerald Field - Fitzgerald Field | 2:15 PM |
| East Haven | | |
| Amity | | |
| WED 10/16 | 11:00 AM | Varsity | Postseason | Normal | Away | | | | | East Shore Athletic Complex - East Shore Park | 9:00 AM |