| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/17 | 4:30 PM | Varsity | League | Normal | Home | New Milford | | | | Weston High School - WHS Stadium Field | |
| Newtown | | |
| Stratford | | |
| TUE 9/24 | 4:30 PM | Varsity | League | Normal | Home | Immaculate | | | | Weston High School - WHS Stadium Field | |
| Notre Dame-Fairfield | | |
| TUE 10/1 | 4:30 PM | Varsity | League | Normal | Away | Brookfield | | | | New Fairfield High School - Track & Field, Cross Country | |
| Bunnell | | |
| New Fairfield | | |
| TUE 10/8 | 4:30 PM | Varsity | League | Normal | Away | Bethel | | | | Joel Barlow High School - Cross Country Course | |
| Joel Barlow | | |
| Masuk | | |