| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 5:00 PM | Varsity | League | Normal | Home | Bunnell | | | | Joel Barlow High School - Cross Country Course | |
| Newtown | | |
| TUE 9/17 | 5:00 PM | Varsity | League | Normal | Away | Kolbe Cathedral | | | | Brookfield High School - BHS Track | |
| Brookfield | | |
| Notre Dame-Fairfield | | |
| TUE 9/24 | 5:00 PM | Varsity | League | Normal | Away | New Milford | | | | New Milford High School - Joe Wiser Stadium - NMHS | |
| Pomperaug | | |
| New Fairfield | | |
| TUE 10/1 | 5:00 PM | Varsity | League | Normal | Away | Stratford | | | | Immaculate High School - Tarrywile | |
| Immaculate | | |
| TUE 10/8 | 5:00 PM | Varsity | League | Normal | Home | Masuk | | | | Joel Barlow High School - Cross Country Course | |
| Bethel | | |
| Weston | | |