| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/3 | 4:00 PM | Varsity | Scrimmage | Normal | Away | Gilbert | | | | Thomaston High School - Black Rock State Park | 2:00 PM |
| Lakeview | | |
| Nonnewaug | | |
| Northwestern | | |
| Shepaug Valley | | |
| Terryville | | |
| Thomaston | | |
| TUE 9/10 | 4:00 PM | Varsity | League | Normal | Away | Terryville | | | | Terryville High School - Track | |
| Lakeview | | |
| TUE 9/24 | 3:45 PM | Varsity | League | Normal | Home | Nonnewaug | | | | Housatonic Valley Regional High - Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) | |
| Gilbert | | |
| TUE 10/1 | 4:00 PM | Varsity | League | Normal | Away | Thomaston | | | | Shepaug Valley High School - Shepaug Valley Middle & High School Cross Country Course | 2:15 PM |
| Shepaug Valley | | |
| TUE 10/8 | 3:30 PM | Varsity | League | Normal | Away | Northwestern | | | | Northwestern Regional H.S. - Track | 2:00 PM |