| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 5:00 PM | Varsity | League | Normal | Home | Brookfield | | | | Great Hollow Lake Field - Cross Country Trail | |
| Immaculate | | |
| New Milford | | |
| TUE 9/17 | 5:00 PM | Varsity | League | Normal | Home | New Fairfield | | | | Great Hollow Lake Field - Cross Country Trail | |
| TUE 9/24 | 5:00 PM | Varsity | League | Normal | Away | Bunnell | | | | Bunnell HS - Bunnell XC Course | |
| Kolbe Cathedral | | |
| TUE 10/8 | 5:00 PM | Varsity | League | Normal | Away | Bethel | | | | Joel Barlow High School - Cross Country Course | |
| Joel Barlow | | |
| Weston | | |