| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/15 | 3:30 PM | Varsity | Non-League | Normal | Away | Coginchaug | | | | Veterans Memorial Park, Middletown, CT - Veterans Memorial Park, Middletown, CT | 2:15 PM |
| Conard | | |
| Morgan | | |
| Naugatuck | | |
| Rocky Hill | | |
| Sacred Heart Academy | | |
| East Catholic | | |
| Maloney | | |
| Avon | | |
| Old Saybrook | | |
| Plainville | | |
| Wethersfield | | |
| Middletown | | |
| Portland | | |
| TUE 9/19 | 3:45 PM | Varsity | League | Normal | Away | Berlin | | | | Rockwell Park - Cross Country Course | 2:15 PM |
| Bristol Central | | |
| TUE 9/26 | 3:45 PM | Varsity | League | Normal | Away | Maloney | | | | Plainville Middle School - Cross Country Course | 2:15 PM |
| Plainville | | |
| TUE 10/3 | 3:45 PM | Varsity | League | Normal | Home | Platt | | | | Lewis Mills High School - Johnnycake Mountain Park | |
| Bristol Eastern | | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Home | Middletown | | | | Lewis Mills High School - Cross Country Course | |