| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/6 | 4:00 PM | Varsity | Non-League | Normal | Away | Lyman Hall | | | | Sheehan High School - Sheehan HS Cross Country Course | |
| Sheehan | | |
| TUE 9/10 | 4:00 PM | Varsity | League | Normal | Away | Lyman Hall | | | | Wharton Brook State Park - Wharton Brook State Park | |
| Jonathan Law | | |
| East Haven | | |
| TUE 9/17 | 4:00 PM | Varsity | League | Normal | Home | Branford | | | | Eisenhower Park - Eisenhower Park | |
| Foran | | |
| Sheehan | | |
| TUE 10/8 | 4:00 PM | Varsity | League | Normal | Away | Career Magnet | | | | Guilford High School - East River Preserve | |
| Guilford | | |
| Shelton | | |