| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 4:30 PM | Varsity | League | Normal | Away | New Milford | | | | New Fairfield High School - Track & Field, Cross Country | 2:15 PM - 1 Bus - Boys and Girls CC Travel Together |
| New Fairfield | | |
| TUE 9/19 | 5:00 PM | Varsity | League | Normal | Home | Notre Dame-Fairfield | | | | Great Hollow Lake Field - Cross Country Trail | |
| Stratford | | |
| Pomperaug | | |
| TUE 9/26 | 4:30 PM | Varsity | League | Normal | Away | Brookfield | | | | Weston High School - WHS Stadium Field | 2:30 PM |
| Weston | | |
| TUE 10/3 | 4:30 PM | Varsity | League | Normal | Home | Newtown | | | | Great Hollow Lake Field - Cross Country Trail | |
| Bethel | | |
| Kolbe Cathedral | | |
| TUE 10/10 | 4:30 PM | Varsity | League | Normal | Away | Bunnell | | | | Bunnell HS - Bunnell XC Course | 2:30 PM - 1 Bus - Boys and Girls Travel Together |
| Joel Barlow | | |
| Immaculate | | |
| WED 10/18 | 3:00 PM | Varsity | League | Normal | Away | Newtown | | | | Bethel High School - BHS track | 12:50 PM |
| Immaculate | | |
| Kolbe Cathedral | | |
| Notre Dame-Fairfield | | |
| Stratford | | |
| Bunnell | | |
| New Fairfield | | |
| New Milford | | |
| Joel Barlow | | |
| Weston | | |
| Bethel | | |
| Pomperaug | | |