| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 10/13 | 4:15 p.m. | Varsity | League | Normal | Home | Bethel | | | | Immaculate High School-Tarrywile | |
| TUE 10/20 | 5:00 p.m. | Varsity | League | Normal | Away | Brookfield | | | | Brookfield High School-BHS Track | |
| FRI 10/23 | 5:00 p.m. | Varsity | League | Normal | Away | Newtown | | | | Reed Intermediate School-Reed Intermediate School XC Trail | |
| TUE 10/27 | 4:15 p.m. | Varsity | League | Normal | Home | NewFairfield | | | | Immaculate High School-Tarrywile | |
| FRI 10/30 | 4:15 p.m. | Varsity | League | Normal | Home | HenryAbbottRVT | | | | Immaculate High School-Tarrywile | |
| TUE 11/3 | 3:30 p.m. | Varsity | League | Normal | Away | Bethel | | | | Bethel High School-DeSantis Field at Bethel High | |
| FRI 11/6 | TBA | Varsity | League | Normal | Away | Tournament Game - Opponent Not Known | | | | TBA | |
| FRI 11/6 | 3:45 p.m. | Varsity | League | Normal | Away | Tournament Game - Opponent Not Known | | | | Bethel High School-DeSantis Field at Bethel High | |