| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/1 | 3:45 PM | Varsity | Scrimmage | Normal | Away | Avon | | | | Cromwell High School - cross country course | |
| Cromwell | | |
| Granby Memorial | | |
| Hale Ray | | |
| TUE 9/12 | 3:45 PM | Varsity | League | Normal | Home | Maloney | | | | Pistol Creek - Pistol Creek | |
| TUE 9/19 | 3:45 PM | Varsity | League | Normal | Away | Bristol Central | | | | Rockwell Park - Cross Country Course | |
| Lewis Mills | | |
| TUE 9/26 | 3:45 PM | Varsity | League | Normal | Away | Middletown | | | | Veterans Memorial Park, Middletown, CT - Veterans Memorial Park, Middletown, CT | |
| Platt | | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Away | Plainville | | | | Plainville Middle School - Cross Country Course | |