| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 9/11 | 4:00 PM | Varsity | League | Normal | Home | Cheshire | | | | Mercy High School - Cross Country Course | |
| Guilford | | |
| Wilbur Cross | | |
| TUE 9/17 | 3:45 PM | Varsity | League | Normal | Away | Jonathan Law | Loss | 19-81 | | Fitzgerald Field - Fitzgerald Field | 1:45 PM |
| Amity | Loss | 19-46 |
| Career Magnet | Loss | |
| MON 10/7 | 3:45 PM | Varsity | League | Normal | Away | Daniel Hand | | | | Wharton Brook State Park - Wharton Brook State Park | 1:45 PM |
| North Haven | | |
| Sheehan | | |