| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 3:45 PM | Varsity | League | Normal | Away | Gilbert | | | | Gilbert School - Cross Country | |
| TUE 10/1 | 4:00 PM | Varsity | League | Normal | Away | Housatonic Regional | | | | Shepaug Valley High School - Shepaug Valley Middle & High School Cross Country Course | |
| Shepaug Valley | | |
| TUE 10/8 | 3:45 PM | Varsity | League | Normal | Away | Nonnewaug | | | | Nonnewaug High School - XC Course | |
| Terryville | | |