| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/14 | 4:00 p.m. | Varsity | League | Normal | Home | Gilbert | | | | Plumb Hill Field Complex-Plumb Hill Track | |
| WED 9/22 | 4:00 p.m. | Varsity | League | Normal | Away | Terryville | | | | Terryville High School-Track | |
| SAT 9/25 | 9:00 a.m. | Varsity | League | Normal | Away | Tournament Game - Opponent Not Known | | | | Winding Trails Center | |
| TUE 9/28 | 4:00 p.m. | Varsity | League | Normal | Away | Nonnewaug | | | | Nonnewaug High School-XC Course | |
| SAT 10/9 | 9:00 a.m. | Varsity | League | Normal | Away | Tournament Game - Opponent Not Known | | | | Wickham Park | |
| TUE 10/12 | 4:00 p.m. | Varsity | League | Normal | Away | ShepaugValley | | | | Shepaug Valley High School-Shepaug Valley Middle & High School Cross Country Course | |
| THU 10/21 | 4:15 p.m. | Varsity | League | Normal | Away | Tournament Game - Opponent Not Known | | | | Black Rock State Park | |