| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/1 | 6:30 PM | Varsity | Scrimmage | Normal | Home | Immaculate | | | | New Fairfield High School - Track & Field, Cross Country | |
| Brookfield | | |
| TUE 9/12 | 5:00 PM | Varsity | League | Normal | Home | New Milford | | | | New Fairfield High School - Track & Field, Cross Country | |
| Masuk | | |
| TUE 9/19 | 5:00 PM | Varsity | League | Normal | Away | Newtown | | | | Reed Intermediate School - Reed Intermediate School XC Trail | |
| Brookfield | | |
| Bunnell | | |
| TUE 9/26 | 5:00 PM | Varsity | League | Normal | Away | Notre Dame-Fairfield | | | | Immaculate High School - Tarrywile | |
| Kolbe Cathedral | | |
| Immaculate | | |
| TUE 10/3 | 5:00 PM | Varsity | League | Normal | Away | Joel Barlow | | | | Joel Barlow High School - Cross Country Course | |
| Pomperaug | | |
| Weston | | |
| TUE 10/10 | 5:00 PM | Varsity | League | Normal | Home | Bethel | | | | New Fairfield High School - Track & Field, Cross Country | |
| Stratford | | |
| WED 10/18 | 3:00 PM | Varsity | League | Normal | Away | Masuk | | | | Bethel High School - BHS track | |
| Joel Barlow | | |
| Pomperaug | | |
| Bunnell | | |
| Immaculate | | |
| Weston | | |
| Notre Dame-Fairfield | | |
| Stratford | | |
| Kolbe Cathedral | | |
| Bethel | | |
| Newtown | | |
| New Milford | | |