| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 5:00 PM | Varsity | League | Normal | Away | Joel Barlow | | | | Joel Barlow High School - Cross Country Course | |
| Newtown | | |
| TUE 9/17 | 5:00 PM | Varsity | League | Normal | Away | Bethel | | | | Bethel High School - BHS track | |
| Immaculate | | |
| Pomperaug | | |
| TUE 9/24 | 5:00 PM | Varsity | League | Normal | Home | Kolbe Cathedral | | | | Bunnell HS - Bunnell XC Course | |
| Masuk | | |
| TUE 10/1 | 5:00 PM | Varsity | League | Normal | Away | Brookfield | | | | New Fairfield High School - Track & Field, Cross Country | |
| New Fairfield | | |
| Weston | | |
| TUE 10/8 | 5:00 PM | Varsity | League | Normal | Home | New Milford | | | | Bunnell HS - Bunnell XC Course | |