| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 9/20 | 3:30 PM | Varsity | Non-League | Normal | Away | New London | | | | Coginchaug Regional High School - Coginchaug Regional HS | |
| East Catholic | | |
| Housatonic Regional | | |
| Maloney | | |
| Coginchaug | | |
| Hale Ray | | |
| Avon | | |
| Holy Cross | | |
| Old Saybrook | | |
| Thomaston | | |
| Valley Regional | | |
| Platt | | |
| Parish Hill | | |
| Portland | | |
| Nonnewaug | | |
| WED 9/27 | 3:30 PM | Varsity | League | Normal | Away | North Branford | | | | John Winthrop Middle School - John Winthrop Middle School | |
| Valley Regional | | |
| Cromwell | | |
| Haddam Killingworth | | |
| Morgan | | |
| WED 10/11 | 3:30 PM | Varsity | League | Normal | Home | Morgan | | | | East Hampton High School - Cross Country Course | |
| WED 10/11 | 3:45 PM | Varsity | League | Normal | Home | Portland | | | | East Hampton High School - Cross Country Course | |