| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 4:30 PM | Varsity | League | Normal | Away | Brookfield | Loss | | | Great Hollow Lake Field - Cross Country Trail | 2:30 PM |
| Immaculate | Loss | |
| Masuk | Loss | 15-42 |
| TUE 9/17 | 4:30 PM | Varsity | League | Normal | Away | Newtown | | | | Weston High School - WHS Track | 2:30 PM |
| Stratford | | |
| Weston | | |
| TUE 9/24 | 4:30 PM | Varsity | League | Normal | Home | Pomperaug | | | | New Milford High School - Joe Wiser Stadium - NMHS | |
| New Fairfield | | |
| Joel Barlow | | |
| TUE 10/1 | 4:30 PM | Varsity | League | Normal | Away | Bethel | | | | Bethel High School - BHS track | 2:30 PM |
| Kolbe Cathedral | | |
| TUE 10/8 | 4:30 PM | Varsity | League | Normal | Away | Bunnell | | | | Bunnell HS - Bunnell XC Course | 2:30 PM |
| Notre Dame Prep | | |
| WED 10/16 | 3:30 PM | Varsity | Postseason | Normal | Away | Notre Dame Prep | | | | Bethel High School - BHS track | |
| Pomperaug | | |
| Weston | | |
| Stratford | | |
| Kolbe Cathedral | | |
| Masuk | | |
| New Fairfield | | |
| Newtown | | |
| Bethel | | |
| Brookfield | | |
| Bunnell | | |
| Joel Barlow | | |
| Immaculate | | |