| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 10/6 | 3:45 p.m. | Varsity | League | Normal | Home | Watertown | | | | Holy Cross | |
| FRI 10/9 | 3:45 p.m. | Varsity | League | Normal | Away | Woodland | | | | Woodland High School-Track | |
| WED 10/14 | 3:45 p.m. | Varsity | League | Normal | Away | Torrington | | | | Torrington High School-THS Cross Country Course | |
| TUE 10/20 | 3:45 p.m. | Varsity | League | Normal | Home | StPaulCatholic | | | | Holy Cross | |
| FRI 10/23 | 3:45 p.m. | Varsity | League | Normal | Away | Oxford | | | | Oxford High School-OHS Wolverine Field (Turf) | |
| WED 11/4 | 3:45 p.m. | Varsity | League | Normal | Away | Wolcott | | | | Bucks Hill (MONTOE) Park-XC Course | |