| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/1 | 5:30 PM | Varsity | Scrimmage | Normal | Away | Wethersfield | | | | Wethersfield High School - Cottone Field | 3:00 PM |
| SAT 9/2 | 9:00 AM | Varsity | Scrimmage | Normal | Away | New Milford | | | | New Fairfield High School - Marty Morgan Field | 7:45 AM |
| Newtown | | |
| Weston | | |
| Bethel | | |
| Ridgefield | | |
| Shepaug Valley | | |
| Amity | | |
| Masuk | | |
| New Fairfield | | |
| TUE 9/5 | Canceled | Varsity | Scrimmage | Canceled | Away | Nonnewaug | | | | Nonnewaug High School - Turf Field | |
| SAT 9/9 | 11:00 AM | Varsity | League | Normal | Away | Hamden | Loss | 1-5 | | Hamden High School - HHS Turf #2 | 9:30 AM |
| THU 9/14 | 3:45 PM | Varsity | Non-League | Normal | Away | Litchfield | Win | 2-1 | | Plumb Hill Field Complex - Field Hockey Field | |
| FRI 9/15 | 5:30 PM | Varsity | Non-League | Normal | Home | Shepaug Valley | Loss | 1-5 | | Brookfield High School - BHS Stadium Field | |
| TUE 9/19 | 4:00 PM | Varsity | League | Normal | Home | Immaculate | Loss | 0-4 | | Brookfield High School - BHS Back Turf | |
| WED 9/20 | 5:30 PM | Varsity | League | Normal | Home | Weston | Loss | 0-3 | | Brookfield High School - BHS Stadium Field | |
| WED 9/27 | 5:00 PM | Varsity | League | Normal | Away | Newtown | Loss | 0-6 | | Treadwell Park - Newtown Treadwell Park | 4:00 PM |
| SAT 9/30 | 10:00 AM | Varsity | League | Normal | Away | Watertown | Loss | 0-3 | | Watertown High - Swift middle turf field | 8:15 AM |
| MON 10/2 | 5:30 PM | Varsity | League | Normal | Home | New Fairfield | Tied | 0-0 | | Brookfield High School - BHS Back Turf | |
| MON 10/9 | 1:30 PM | Varsity | Non-League | Normal | Home | Hamden | Loss | 1-7 | | Brookfield High School - BHS Back Turf | |
| WED 10/11 | 5:45 PM | Varsity | League | Normal | Away | Bethel | Win | 2-1 | | Bethel High School - Middle School Turf Soccer Field | 3:45 PM |
| THU 10/12 | 7:00 PM | Varsity | Non-League | Normal | Home | Litchfield | Win | 9-0 | | Brookfield High School - BHS Stadium Field | |
| FRI 10/13 | 7:00 PM | Varsity | League | Normal | Away | Joel Barlow | Loss | 0-5 | | Joel Barlow High School - Field I (Stadium) | 4:00 PM |
| MON 10/16 | 5:00 PM | Varsity | League | Normal | Home | Pomperaug | Loss | 0-6 | | Brookfield High School - BHS Back Turf | |
| WED 10/18 | 5:30 PM | Varsity | League | Normal | Away | New Milford | Loss | 0-3 | | New Milford High School - Joe Wiser Stadium - NMHS | 4:15 PM |
| FRI 10/20 | 4:00 PM | Varsity | Non-League | Normal | Away | Bethel | Tied | 1-1 | | Bethel High School - Middle School Turf Soccer Field | |
| MON 10/23 | 5:00 PM | Varsity | League | Normal | Home | Masuk | Loss | 1-5 | | Brookfield High School - BHS Stadium Field | |