| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 9/11 | 4:00 PM | Varsity | League | Normal | Away | Guilford | | | | Mercy High School - Cross Country Course | |
| Wilbur Cross | | |
| Xavier | | |
| TUE 9/17 | 4:00 PM | Varsity | League | Normal | Home | Daniel Hand | | | | Cheshire Park - Field 1 | |
| East Haven | | |
| West Haven | | |
| TUE 10/8 | 3:30 PM | Varsity | League | Normal | Away | Jonathan Law | | | | Carrigan Middle School - Baseball Field | 2:15 PM |
| Branford | | |
| Notre Dame-West Haven | | |
| THU 10/10 | 4:00 PM | Varsity | League | Normal | Away | Lyman Hall | | | | Wharton Brook State Park - Wharton Brook State Park | |