| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/6 | 3:00 PM | Varsity | Non-League | Normal | Away | | | | | Wharton Brook State Park - Wharton Brook State Park | 2:15 PM |
| SAT 9/7 | 12:01 AM | Varsity | League | Normal | Away | | | | | TBA | 12:01 AM |
| WED 9/11 | 4:00 PM | Varsity | League | Normal | Away | Amity | Loss | 0-41 | | EISENHOWER PARK - EISENHOWER PARK | 2:15 PM |
| Foran | Loss | 0-54 |
| Sacred Heart Academy | Loss | 0-34 |
| TUE 9/17 | 3:45 PM | Varsity | League | Normal | Away | Lyman Hall | | | | Hamden Middle School - Back Field | 2:15 PM |
| Guilford | | |
| Hamden | | |
| MON 9/23 | 4:00 PM | Varsity | Non-League | Normal | Away | Jonathan Law | | | | Eisenhower Park - Eisenhower Park | 2:15 PM |
| East Haven | | |
| Foran | | |
| Branford | | |
| Lauralton Hall | | |
| Amity | | |
| Shelton | | |
| West Haven | | |
| Wilbur Cross | | |
| Sacred Heart Academy | | |
| SAT 9/28 | 8:00 AM | Varsity | Non-League | Normal | Away | | | | | Wickham Park | 12:01 AM |
| WED 10/2 | 3:45 PM | Varsity | League | Normal | Away | | | | | TBA | 2:15 PM |
| MON 10/7 | 3:45 PM | Varsity | League | Normal | Home | Daniel Hand | | | | Wharton Brook State Park - Wharton Brook State Park | |
| Mercy | | |
| Sheehan | | |
| WED 10/16 | 12:01 AM | Varsity | Postseason | Normal | Away | | | | | East Shore Athletic Complex | 12:00 PM |