| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 9/11 | 4:00 PM | Varsity | League | Normal | Away | Career Magnet | | | | Sheehan High School - Sheehan HS Cross Country Course | |
| Sheehan | | |
| West Haven | | |
| TUE 9/17 | 4:00 PM | Varsity | League | Normal | Away | Wilbur Cross | | | | Shelton High School - Track | |
| Shelton | | |
| Sacred Heart Academy | | |
| MON 10/7 | 3:45 PM | Varsity | League | Normal | Away | Amity | | | | Fitzgerald Field - Fitzgerald Field | |
| East Haven | | |
| Hamden | | |