| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 9/14 | 5:00 p.m. | Varsity | League | Normal | Home | KolbeCathedral | | | | New Fairfield High School-Track & Field, Cross Country | |
| SAT 9/17 | 9:00 a.m. | Varsity | League | Normal | Away | Wilton | | | | Allen's Meadow-XC Course | |
| TUE 9/20 | 5:00 p.m. | Varsity | League | Normal | Away | Immaculate | | | | Immaculate High School-Tarrywile | |
| WED 9/28 | 5:00 p.m. | Varsity | League | Normal | Away | Newtown | | | | Reed Intermediate School-Reed Intermediate School XC Trail | |
| MON 10/3 | 5:00 p.m. | Varsity | League | Normal | Away | Pomperaug | | | | Pomperaug High School-Cross Country Course | |
| TUE 10/11 | 5:00 p.m. | Varsity | League | Normal | Home | Brookfield | | | | New Fairfield High School-Track & Field, Cross Country | |
| WED 10/19 | 4:00 p.m. | Varsity | League | Normal | Away | Tournament Game - Opponent Not Known | | | | Bethel High School-BHS track | |