| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/14 | 3:45 p.m. | Varsity | League | Normal | Home | Wolcott | | | | Woodland High School-Track | |
| SAT 9/18 | 9:30 a.m. | Varsity | League | Normal | Away | Wilton | | | | Allen's Meadow-XC Course | |
| TUE 9/21 | 5:15 p.m. | Varsity | League | Normal | Away | Torrington | | | | Torrington High School-THS Cross Country Course | |
| WED 9/29 | 3:45 p.m. | Varsity | League | Normal | Away | HolyCross | | | | Holy Cross | |
| TUE 10/5 | 3:00 p.m. | Varsity | League | Normal | Away | Watertown | | | | Veterans Memorial Park-Veterans Park XC Course | |
| TUE 10/12 | 3:15 p.m. | Varsity | League | Normal | Home | Derby | | | | Woodland High School-Track | |