| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 3:45 PM | Varsity | League | Normal | Home | Plainville | | | | Hubbard Park - Tennis courts | |
| Bristol Central | | |
| WED 9/20 | 3:30 PM | Varsity | Non-League | Normal | Away | New London | | | | Coginchaug Regional High School - Coginchaug Regional HS | |
| Housatonic Regional | | |
| East Catholic | | |
| Avon | | |
| Parish Hill | | |
| Coginchaug | | |
| Nonnewaug | | |
| East Hampton | | |
| Hale Ray | | |
| Portland | | |
| Holy Cross | | |
| Maloney | | |
| Old Saybrook | | |
| Thomaston | | |
| Valley Regional | | |
| TUE 9/26 | 3:45 PM | Varsity | League | Normal | Away | Berlin | | | | Veterans Memorial Park, Middletown, CT - Veterans Memorial Park, Middletown, CT | |
| Middletown | | |
| TUE 10/3 | 3:45 PM | Varsity | League | Normal | Away | Lewis Mills | | | | Lewis Mills High School - Johnnycake Mountain Park | |
| Bristol Eastern | | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Away | Wilcox Tech | | | | Hubbard Park - Hubbard Park Band Shell | |
| Maloney | | |