| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 4:30 PM | Varsity | League | Normal | Away | Bunnell | | | | Seaside Park - Seaside Park | 2:30 PM - 1 Bus |
| Kolbe Cathedral | | |
| Weston | | |
| TUE 9/19 | 5:00 PM | Varsity | League | Normal | Away | Masuk | | | | Great Hollow Lake Field - Cross Country Trail | 2:30 PM - 1 Bus |
| Notre Dame-Fairfield | | |
| Pomperaug | | |
| TUE 9/26 | 5:00 PM | Varsity | League | Normal | Home | Joel Barlow | | | | Wooster Middle School Field - Wooster Middle School Field | |
| Newtown | | |
| TUE 10/3 | 4:30 PM | Varsity | League | Normal | Away | Brookfield | | | | Brookfield High School - BHS Track | 2:15 PM - 1 Bus |
| Immaculate | | |
| New Milford | | |
| TUE 10/10 | 4:30 PM | Varsity | League | Normal | Away | Bethel | | | | New Fairfield High School - Track & Field, Cross Country | 1:45 PM - 1 Bus |
| New Fairfield | | |
| FRI 10/13 | 3:30 PM | Varsity | Non-League | Normal | Away | Jonathan Law | | | | Eisenhower Park - Eisenhower Park | 2:15 PM - 1 Bus |
| Platt Tech | | |
| West Haven | | |
| WED 10/18 | 3:00 PM | Varsity | League | Normal | Away | Bethel | | | | Bethel High School - BHS track | 1:00 PM - 1 Bus |
| Bunnell | | |
| Immaculate | | |
| Joel Barlow | | |
| Kolbe Cathedral | | |
| Masuk | | |
| New Fairfield | | |
| New Milford | | |
| Newtown | | |
| Notre Dame-Fairfield | | |
| Pomperaug | | |
| Weston | | |