| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 3:30 PM | Varsity | League | Normal | Away | Nonnewaug | | | | Northwestern Regional H.S. - Track | 2:00 PM |
| Northwestern | | |
| TUE 9/24 | 4:00 PM | Varsity | League | Normal | Home | Terryville | | | | Shepaug Valley High School - Shepaug Valley Middle & High School Cross Country Course | |
| TUE 10/1 | 4:00 PM | Varsity | League | Normal | Home | Thomaston | | | | Shepaug Valley High School - Shepaug Valley Middle & High School Cross Country Course | |
| Housatonic Regional | | |
| TUE 10/8 | 3:45 PM | Varsity | League | Normal | Away | Litchfield | | | | Gilbert School - Cross Country | 2:00 PM |
| Gilbert | | |