| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 4:30 PM | Varsity | League | Normal | Home | Bethel | | | | Wooster Middle School Field - Wooster Middle School Field | |
| New Fairfield | | |
| Notre Dame-Fairfield | | |
| TUE 9/17 | 4:30 PM | Varsity | League | Normal | Away | New Milford | | | | Weston High School - WHS Stadium Field | 2:15 PM - 1 Bus |
| Newtown | | |
| Weston | | |
| TUE 10/1 | 4:30 PM | Varsity | League | Normal | Away | Immaculate | | | | Immaculate High School - Tarrywile | 2:30 PM - 1 Bus |
| Joel Barlow | | |
| TUE 10/8 | 4:30 PM | Varsity | League | Normal | Away | Brookfield | | | | Brookfield High School - BHS Track | 2:15 PM - 1 Bus |
| Pomperaug | | |