| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 8/29 | 6:00 PM | Varsity | Scrimmage | Normal | Home | Shelton | | | | Joel Barlow High School - Field I (Stadium) | |
| TUE 9/5 | 6:00 PM | Varsity | Scrimmage | Normal | Away | Amity | | | | Amity Regional High School - William Johnson Stadium Field | 2:15 PM - 1 Bus |
| THU 9/7 | 7:00 PM | Varsity | Non-League | Normal | Home | New Milford | Loss | 1-2 | | Joel Barlow High School - Field I (Stadium) | |
| SAT 9/9 | 1:30 PM | Varsity | Non-League | Normal | Home | Weston | Loss | 0-1 | | Joel Barlow High School - Field J (Competition Field) | |
| THU 9/14 | 4:00 PM | Varsity | League | Normal | Home | New Fairfield | Win | 3-2 | | Joel Barlow High School - Field J (Competition Field) | |
| MON 9/18 | 6:00 PM | Varsity | League | Normal | Away | Bethel | Tied | 1-1 | | Bethel High School - Middle School soccer field | |
| WED 9/20 | 7:00 PM | Varsity | League | Normal | Home | Pomperaug | Loss | 1-3 | | Joel Barlow High School - Field I (Stadium) | |
| SAT 9/23 | 12:00 PM | Varsity | Non-League | Normal | Home | Stamford | Win | 2-1 | | Joel Barlow High School - Field I (Stadium) | |
| WED 9/27 | 5:30 PM | Varsity | League | Normal | Away | New Milford | Tied | 0-0 | | New Milford High School - Joe Wiser Stadium - NMHS | |
| THU 9/28 | 7:00 PM | Varsity | Non-League | Normal | Away | Masuk | Loss | 1-2 | | Masuk High School - Benedict Stadium Field @ Masuk HS | 5:30 PM - 1 Bus |
| MON 10/2 | 6:45 PM | Varsity | League | Normal | Home | Masuk | Loss | 2-3 | | Joel Barlow High School - Field I (Stadium) | |
| SAT 10/7 | 11:00 AM | Varsity | Non-League | Normal | Home | Bethel | Win | 3-0 | | Joel Barlow High School - Field I (Stadium) | |
| WED 10/11 | 5:30 PM | Varsity | League | Normal | Away | Weston | Loss | 0-3 | | Weston High School - WHS Lower Turf Field | |
| FRI 10/13 | 7:00 PM | Varsity | League | Normal | Home | Brookfield | Win | 5-0 | | Joel Barlow High School - Field I (Stadium) | |
| MON 10/16 | 7:00 PM | Varsity | League | Normal | Home | Newtown | Win | 2-1 | | Joel Barlow High School - Field I (Stadium) | |
| WED 10/18 | 5:45 PM | Varsity | League | Normal | Away | New Fairfield | Loss | 0-1 | | New Fairfield High School - Marty Morgan Field | |
| MON 10/23 | 7:00 PM | Varsity | League | Normal | Home | Immaculate | Loss | 1-4 | | Joel Barlow High School - Field I (Stadium) | |
| THU 10/26 | 6:00 PM | Varsity | Postseason | Normal | Away | Newtown | Loss | 1-4 | | Newtown High School - Blue and Gold Stadium | 4:15 PM - 1 Bus |
| WED 11/1 | 3:45 PM | Varsity | Scrimmage | Normal | Home | Weston | | | | Joel Barlow High School - Field J | |
| TUE 11/7 | 4:00 PM | Varsity | Postseason | Normal | Away | Daniel Hand | Loss | 0-4 | | Daniel Hand High School - Turf Field | 1:30 PM - 1 Bus |