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