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