| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 9/11 | 4:00 PM | Varsity | League | Normal | Away | Hillhouse | | | | Sheehan High School - Sheehan HS Cross Country Course | |
| Sheehan | | |
| West Haven | | |
| TUE 9/17 | 3:45 PM | Varsity | League | Normal | Away | Xavier | | | | Fitzgerald Field - Fitzgerald Field | |
| Jonathan Law | | |
| Amity | | |
| TUE 10/8 | 4:00 PM | Varsity | League | Normal | Away | Fairfield Prep | | | | Guilford High School - East River Preserve | |
| Guilford | | |
| Shelton | | |