| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 4:30 PM | Varsity | League | Normal | Home | Bunnell | | | | Seaside Park - Seaside Park | |
| Stratford | | |
| Weston | | |
| TUE 9/19 | 4:30 PM | Varsity | League | Normal | Away | Joel Barlow | | | | Joel Barlow High School - Cross Country Course | |
| New Milford | | |
| TUE 9/26 | 4:30 PM | Varsity | League | Normal | Away | Immaculate | | | | Immaculate High School - Tarrywile | |
| New Fairfield | | |
| Notre Dame-Fairfield | | |
| TUE 10/3 | 4:30 PM | Varsity | League | Normal | Away | Bethel | | | | Great Hollow Lake Field - Cross Country Trail | |
| Masuk | | |
| Newtown | | |
| TUE 10/10 | 4:30 PM | Varsity | League | Normal | Home | Brookfield | | | | Seaside Park - Seaside Park | |
| Pomperaug | | |
| WED 10/18 | 3:00 PM | Varsity | League | Normal | Away | Bethel | | | | Bethel High School - BHS track | |
| Bunnell | | |
| Immaculate | | |
| Joel Barlow | | |
| Masuk | | |
| New Fairfield | | |
| New Milford | | |
| Newtown | | |
| Notre Dame-Fairfield | | |
| Pomperaug | | |
| Stratford | | |
| Weston | | |