| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 5:00 PM | Varsity | League | Normal | Away | Bethel | | | | Wooster Middle School Field - Wooster Middle School Field | |
| New Fairfield | | |
| Stratford | | |
| TUE 9/17 | 5:00 PM | Varsity | League | Normal | Away | Brookfield | | | | Brookfield High School - BHS Track | |
| Joel Barlow | | |
| Kolbe Cathedral | | |
| TUE 9/24 | 5:00 PM | Varsity | League | Normal | Away | Immaculate | | | | Weston High School - WHS Stadium Field | |
| Weston | | |