| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 8/30 | 6:00 PM | Varsity | Scrimmage | Normal | Home | Brookfield | | | | New Fairfield High School - Track & Field, Cross Country | |
| Danbury | | |
| Immaculate | | |
| TUE 9/10 | 5:00 PM | Varsity | League | Normal | Away | Bethel | | | | Wooster Middle School Field - Wooster Middle School Field | |
| Notre Dame Prep | | |
| Stratford | | |
| TUE 9/17 | 5:00 PM | Varsity | League | Normal | Away | Masuk | | | | Great Hollow Lake Field - Cross Country Trail | |
| TUE 9/24 | 5:00 PM | Varsity | League | Normal | Away | Joel Barlow | | | | New Milford High School - Joe Wiser Stadium - NMHS | |
| New Milford | | |
| Pomperaug | | |
| TUE 10/1 | 5:00 PM | Varsity | League | Normal | Home | Brookfield | | | | New Fairfield High School - Track & Field, Cross Country | |
| Bunnell | | |
| Weston | | |
| TUE 10/8 | 4:30 PM | Varsity | League | Normal | Away | Immaculate | | | | Seaside Park - Seaside Park | |
| Kolbe Cathedral | | |
| Newtown | | |
| WED 10/16 | 4:00 PM | Varsity | Postseason | Normal | Away | Bethel | | | | Bethel High School - BHS track | |
| Brookfield | | |
| Bunnell | | |
| Immaculate | | |
| Joel Barlow | | |
| Kolbe Cathedral | | |
| Stratford | | |
| Weston | | |
| Masuk | | |
| New Milford | | |
| Newtown | | |
| Notre Dame Prep | | |
| Pomperaug | | |