| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/6 | 3:30 p.m. | Varsity | League | Normal | Away | Middletown | | | | Veterans Memorial Park, Middletown, CT | |
| TUE 9/10 | 3:45 p.m. | Varsity | League | Normal | Away | BristolCentral | | | | Rockwell Park-Cross Country Course | |
| FRI 9/13 | 3:45 p.m. | Varsity | League | Normal | Away | NathanHaleRay | | | | Nathan Hale Ray High School-HS XC Course | |
| TUE 9/17 | 3:45 p.m. | Varsity | League | Normal | Home | Berlin | | | | Plainville Middle School-Cross Country Course | |
| TUE 10/1 | 3:45 p.m. | Varsity | League | Normal | Away | Maloney | | | | Hubbard Park-Hubbard Park Band Shell | |
| TUE 10/8 | 4:00 p.m. | Varsity | League | Normal | Home | LewisMills | | | | Plainville Middle School-Cross Country Course | |