| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 5:00 PM | Varsity | League | Normal | Away | Bunnell | | | | Joel Barlow High School - Cross Country Course | |
| Joel Barlow | | |
| TUE 9/17 | 5:00 PM | Varsity | League | Normal | Away | New Milford | | | | Weston High School - WHS Track | 2:45 PM - 1 Bus |
| Stratford | | |
| Weston | | |
| TUE 9/24 | 5:00 PM | Varsity | League | Normal | Home | Brookfield | | | | Reed Intermediate School - Reed Intermediate School XC Trail | |
| Bethel | | |
| TUE 10/1 | 5:00 PM | Varsity | League | Normal | Away | Masuk | | | | Settlers Park - Cross Country Course | |
| Pomperaug | | |
| Notre Dame Prep | | |
| TUE 10/8 | 4:30 PM | Varsity | League | Normal | Away | New Fairfield | | | | Seaside Park - Seaside Park | 2:45 PM - 1 Bus |
| Kolbe Cathedral | | |
| Immaculate | | |
| WED 10/16 | 4:00 PM | Varsity | Postseason | Normal | Away | Joel Barlow | | | | Bethel High School - BHS track | |
| Bunnell | | |
| Immaculate | | |
| Brookfield | | |
| WED 10/16 | 12:01 AM | Varsity | League | Normal | Away | | | | | Bethel High School - TBA | 12:01 AM |
| WED 10/16 | 4:00 PM | Varsity | Postseason | Normal | Away | Bethel | | | | Bethel High School - BHS track | |
| Masuk | | |
| Kolbe Cathedral | | |
| New Milford | | |
| New Fairfield | | |
| Notre Dame Prep | | |
| Pomperaug | | |
| Stratford | | |
| Weston | | |