| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 5:00 p.m. | Varsity | League | Normal | Away | Pomperaug | | | | Pomperaug High School-Cross Country Course | |
| TUE 9/17 | 5:00 p.m. | Varsity | League | Normal | Away | NewFairfield | | | | New Fairfield High-Track & Field, Cross Country | |
| TUE 9/24 | 5:00 p.m. | Varsity | League | Normal | Away | Masuk | | | | Great Hollow Lake Fields at Wolfe Park-Cross Country Trail | |
| WED 10/2 | 5:00 p.m. | Varsity | League | Normal | Home | Bethel | | | | Joel Barlow High School-Cross Country Course | |
| MON 10/7 | 5:00 p.m. | Varsity | League | Normal | Home | KolbeCathedral | | | | Joel Barlow High School-Cross Country Course | |