| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 8/30 | 6:00 PM | Varsity | Scrimmage | Normal | Away | Danbury | | | | Danbury High School - Stadium Turf Field | 4:45 PM - 1 Bus |
| SAT 9/2 | 9:00 AM | Varsity | Scrimmage | Normal | Away | Amity | | | | New Fairfield High School - Marty Morgan Field | 7:45 AM - 1 Bus |
| Brookfield | | |
| Masuk | | |
| New Fairfield | | |
| New Milford | | |
| Newtown | | |
| Ridgefield | | |
| Shepaug Valley | | |
| Weston | | |
| THU 9/7 | 7:00 PM | Varsity | Non-League | Normal | Away | New Fairfield | Tied | 0-0 | | New Fairfield High School - Marty Morgan Field | 2:30 PM - 1 Bus |
| SAT 9/9 | 10:00 AM | Varsity | Non-League | Normal | Away | Trumbull | Loss | 0-7 | | Trumbull High School - Cork Field | 8:45 AM - 1 Bus |
| WED 9/13 | 4:00 PM | Varsity | Non-League | Normal | Home | Immaculate | Loss | 0-3 | | Bethel High School - Middle School Turf Soccer Field | |
| MON 9/18 | 6:00 PM | Varsity | League | Normal | Home | Joel Barlow | Tied | 1-1 | | Bethel High School - Middle School soccer field | |
| WED 9/20 | 4:00 PM | Varsity | League | Normal | Away | Immaculate | Loss | 0-7 | | Immaculate High School - Rogers Park, Danbury | 2:30 PM - 1 Bus |
| WED 9/27 | 7:30 PM | Varsity | League | Normal | Away | Pomperaug | Loss | 0-8 | | Pomperaug High School - Stadium | 4:45 PM - 1 Bus |
| MON 10/2 | 4:00 PM | Varsity | League | Normal | Home | New Milford | Loss | 0-4 | | Bethel High School - Middle School soccer field | |
| WED 10/4 | 7:00 PM | Varsity | League | Normal | Away | Masuk | Loss | 0-6 | | Masuk High School - Benedict Stadium Field @ Masuk HS | 4:15 PM - 1 Bus |
| SAT 10/7 | 11:00 AM | Varsity | Non-League | Normal | Away | Joel Barlow | Loss | 0-3 | | Joel Barlow High School - Field I (Stadium) | 8:45 AM - 1 Bus |
| WED 10/11 | 5:45 PM | Varsity | League | Normal | Home | Brookfield | Loss | 1-2 | | Bethel High School - Middle School Turf Soccer Field | |
| SAT 10/14 | 10:00 AM | Varsity | Non-League | Normal | Away | Weston | Loss | 0-5 | | Weston High School - WHS Lower Turf Field | 8:45 AM - 1 Bus |
| MON 10/16 | 6:30 PM | Varsity | League | Normal | Home | Weston | Loss | 0-1 | | Bethel High School - Middle School Turf Soccer Field | |
| WED 10/18 | 6:00 PM | Varsity | League | Normal | Away | Newtown | Loss | 0-7 | | Newtown High School - Blue and Gold Stadium | 2:30 PM - 1 Bus |
| FRI 10/20 | 4:00 PM | Varsity | Non-League | Normal | Home | Brookfield | Tied | 1-1 | | Bethel High School - Middle School Turf Soccer Field | |
| MON 10/23 | 4:00 PM | Varsity | League | Normal | Home | New Fairfield | Loss | 0-2 | | Bethel High School - Middle School Turf Soccer Field | |
| TUE 10/24 | 4:00 PM | Varsity | Non-League | Normal | Home | Nonnewaug | Win | 2-1 | | Bethel High School - Hunt Field at Bethel HS | |