| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 4:30 PM | Varsity | League | Normal | Away | Brookfield | | | | Great Hollow Lake Field - Cross Country Trail | |
| Masuk | | |
| New Milford | | |
| TUE 9/17 | 4:30 PM | Varsity | League | Normal | Away | Bunnell | | | | Bethel High School - BHS track | |
| Bethel | | |
| Pomperaug | | |
| TUE 9/24 | 4:30 PM | Varsity | League | Normal | Away | Weston | | | | Weston High School - WHS Stadium Field | |
| Notre Dame-Fairfield | | |
| TUE 10/1 | 4:30 PM | Varsity | League | Normal | Home | Stratford | | | | Immaculate High School - Tarrywile | |
| Joel Barlow | | |
| TUE 10/8 | 4:00 PM | Varsity | League | Normal | Away | New Fairfield | | | | Seaside Park - Seaside Park | |
| Newtown | | |
| Kolbe Cathedral | | |