| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 10/1 | 6:30 p.m. | Varsity | League | Normal | Away | Brookfield | Tied | 2-2 | | Brookfield High School-BHS Stadium Field | |
| SAT 10/3 | 10:00 a.m. | Varsity | League | Normal | Away | Masuk | Win | 3-0 | | Masuk High School-Benedict Stadium Field @ Masuk HS | |
| THU 10/8 | 6:00 p.m. | Varsity | League | Normal | Home | Pomperaug | Loss | 0-2 | | New Fairfield High-Rebel Turf | |
| SAT 10/10 | 2:00 p.m. | Varsity | League | Normal | Away | Immaculate | Win | 2-0 | | Immaculate High School-Mustang Valley | |
| TUE 10/13 | 4:15 p.m. | Varsity | League | Normal | Home | NewMilford | Tied | 1-1 | | New Fairfield High-Rebel Turf | |
| THU 10/15 | 4:15 p.m. | Varsity | League | Normal | Home | Newtown | Loss | 1-3 | | New Fairfield High-Rebel Turf | |
| TUE 10/27 | 6:00 p.m. | Varsity | League | Normal | Home | Masuk | Win | 1-0 | | New Fairfield High-Rebel Turf | |
| THU 10/29 | 4:15 p.m. | Varsity | League | Normal | Home | Immaculate | Loss | 1-3 | | New Fairfield High-Rebel Turf | |
| MON 11/2 | 4:15 p.m. | Varsity | League | Normal | Away | Bethel | Loss | 1-3 | | Bethel High School-DeSantis Field at Bethel High | |
| TUE 11/3 | 4:15 p.m. | Varsity | League | Normal | Away | NewMilford | Tied | 0-0 | | New Milford High School-Joe Wiser Stadium - NMHS | |
| THU 11/5 | 5:00 p.m. | Varsity | League | Normal | Away | Pomperaug | Loss | 1-6 | | Pomperaug High School-Stadium | |
| SAT 11/7 | 10:00 a.m. | Varsity | League | Normal | Home | Brookfield | Loss | 0-3 | | New Fairfield High-Rebel Turf | |