| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 10/1 | 3:45 p.m. | Varsity | League | Normal | Home | NorthwestCatholic | | | | Bloomfield High School-Cross Country Course | |
| WED 10/7 | 3:45 p.m. | Varsity | League | Normal | Home | Windsor | | | | Bloomfield High School-Cross Country Course | |
| WED 10/14 | 3:45 p.m. | Varsity | League | Normal | Away | Enfield | | | | Powder Hollow - Dust House Road-Cross Country Course | |
| THU 10/22 | 3:45 p.m. | Varsity | League | Normal | Home | Conard | | | | Bloomfield High School-Cross Country Course | |
| MON 10/26 | 3:45 p.m. | Varsity | League | Normal | Away | HartfordPublic | | | | Elizabeth Park | |
| WED 11/4 | 3:45 p.m. | Varsity | League | Normal | Away | Simsbury | | | | Stratton Brook State Park | |
| FRI 11/6 | 3:45 p.m. | Varsity | League | Normal | Away | WmHall | | | | Hall High School-Stadium (Track) | |