| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/1 | 4:30 PM | Varsity | Scrimmage | Normal | Home | Danbury | | | | Pomperaug High School - Cross Country Course | |
| TUE 9/12 | 4:30 PM | Varsity | League | Normal | Home | Immaculate | | | | Pomperaug High School - Cross Country Course | |
| Newtown | | |
| TUE 9/19 | 5:00 PM | Varsity | League | Normal | Away | Notre Dame-Fairfield | | | | Great Hollow Lake Field - Cross Country Trail | 3:00 PM - Share bus w/ girls |
| Stratford | | |
| Masuk | | |
| TUE 9/26 | 4:30 PM | Varsity | League | Normal | Home | Bethel | | | | Pomperaug High School - Cross Country Course | |
| Bunnell | | |
| New Milford | | |
| TUE 10/3 | 4:30 PM | Varsity | League | Normal | Away | Weston | | | | Joel Barlow High School - Cross Country Course | 2:30 PM - Share bus w/ girls |
| New Fairfield | | |
| Joel Barlow | | |
| TUE 10/10 | 4:30 PM | Varsity | League | Normal | Away | Kolbe Cathedral | | | | Seaside Park - Seaside Park | 2:30 PM - Share bus w/ girls |
| Brookfield | | |
| WED 10/18 | 3:00 PM | Varsity | League | Normal | Away | Bunnell | | | | Bethel High School - BHS track | 1:15 PM - Share bus w/ girls |
| Bethel | | |
| Immaculate | | |
| Joel Barlow | | |
| Masuk | | |
| Kolbe Cathedral | | |
| New Fairfield | | |
| New Milford | | |
| Newtown | | |
| Notre Dame-Fairfield | | |
| Stratford | | |
| Weston | | |