| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 4:30 PM | Varsity | League | Normal | Home | Brookfield | Win | | | Great Hollow Lake Field - Cross Country Trail | |
| Immaculate | Win | |
| New Milford | Win | 42-15 |
| TUE 9/17 | 4:30 PM | Varsity | League | Normal | Home | New Fairfield | Win | 47-15 | | Great Hollow Lake Field - Cross Country Trail | |
| TUE 9/24 | 4:30 PM | Varsity | League | Normal | Away | Kolbe Cathedral | | | | Bunnell HS - Bunnell XC Course | |
| Stratford | | |
| Bunnell | | |
| TUE 10/1 | 4:30 PM | Varsity | League | Normal | Away | Notre Dame Prep | | | | Settlers Park - Cross Country Course | |
| Pomperaug | | |
| Newtown | | |
| TUE 10/8 | 4:30 PM | Varsity | League | Normal | Away | Joel Barlow | | | | Joel Barlow High School - Cross Country Course | |
| Bethel | | |
| Weston | | |
| WED 10/16 | 3:30 PM | Varsity | Postseason | Normal | Away | Weston | | | | Bethel High School - BHS track | |
| Pomperaug | | |
| Stratford | | |
| Bethel | | |
| Brookfield | | |
| Bunnell | | |
| Joel Barlow | | |
| Immaculate | | |
| Notre Dame Prep | | |
| New Milford | | |
| Newtown | | |
| Kolbe Cathedral | | |
| New Fairfield | | |