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