| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 4:30 PM | Varsity | League | Normal | Home | Putnam | | | | Plainfield High School Athletic Upper Complex - Cross Country Course | |
| St. Bernard | | |
| TUE 9/17 | 3:45 PM | Varsity | League | Normal | Away | New London | | | | Caulkins Park - Caulkins Park | |
| TUE 10/1 | 4:30 PM | Varsity | League | Normal | Home | Montville | | | | Plainfield High School Athletic Upper Complex - Cross Country Course | |
| Windham | | |
| TUE 10/8 | 4:30 PM | Varsity | League | Normal | Home | Tourtellotte | | | | Plainfield High School Athletic Upper Complex - Cross Country Course | |
| Lyman Memorial | | |