| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 5:00 PM | Varsity | League | Normal | Away | Kolbe Cathedral | | | | Settlers Park - Cross Country Course | 2:45 PM |
| Pomperaug | | |
| SAT 9/14 | 9:00 AM | Varsity | Non-League | Normal | Away | | | | | Not Listed | 7:45 AM |
| TUE 9/17 | 5:00 PM | Varsity | League | Normal | Home | New Milford | | | | Weston High School - WHS Track | |
| Newtown | | |
| Stratford | | |
| TUE 9/24 | 5:00 PM | Varsity | League | Normal | Home | Notre Dame Prep | | | | Weston High School - WHS Track | |
| Immaculate | | |
| TUE 10/1 | 5:00 PM | Varsity | League | Normal | Away | New Fairfield | | | | New Fairfield High School - Track & Field, Cross Country | 2:45 PM |
| Brookfield | | |
| Bunnell | | |
| TUE 10/8 | 5:00 PM | Varsity | League | Normal | Away | Bethel | | | | Joel Barlow High School - Cross Country Course | 2:45 PM |
| Masuk | | |
| Joel Barlow | | |
| WED 10/16 | 4:00 PM | Varsity | Postseason | Normal | Away | Pomperaug | | | | Bethel High School - BHS track | 2:45 PM |
| Stratford | | |
| Notre Dame Prep | | |
| Newtown | | |
| New Fairfield | | |
| New Milford | | |
| Joel Barlow | | |
| Kolbe Cathedral | | |
| Masuk | | |
| Brookfield | | |
| Bethel | | |
| Bunnell | | |
| Immaculate | | |