| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/14 | 5:00 p.m. | Varsity | League | Normal | Away | Bunnell | | | | Bunnell HS-Bunnell XC Course | |
| TUE 9/21 | 4:30 p.m. | Varsity | League | Normal | Away | Pomperaug | | | | Pomperaug High School-Cross Country Course | |
| TUE 9/28 | 5:00 p.m. | Varsity | League | Normal | Home | Immaculate | | | | Wooster Middle School Field | |
| TUE 10/5 | 4:30 p.m. | Varsity | League | Normal | Away | Newtown | | | | Reed Intermediate School-Reed Intermediate School XC Trail | |
| FRI 10/8 | 4:00 p.m. | Varsity | League | Normal | Home | Bunnell | | | | Wooster Middle School Field | |
| TUE 10/12 | 4:30 p.m. | Varsity | League | Normal | Away | JoelBarlow | | | | Joel Barlow High School-Cross Country Course | |