| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 9/2 | 9:00 AM | Varsity | Scrimmage | Normal | Away | Amity | | | | New Fairfield High School - Marty Morgan Field | 7:45 AM - 1 Bus |
| Bethel | | |
| Brookfield | | |
| Masuk | | |
| New Fairfield | | |
| New Milford | | |
| Ridgefield | | |
| Shepaug Valley | | |
| Weston | | |
| SAT 9/9 | 10:00 AM | Varsity | Non-League | Normal | Away | Fairfield Ludlowe | Loss | 0-3 | | Fairfield Ludlowe High School - Taft Field | 8:20 AM - 1 Bus |
| WED 9/13 | 4:45 PM | Varsity | Non-League | Normal | Home | New Milford | Win | 3-0 | | Newtown High School - Blue and Gold Stadium | |
| FRI 9/15 | 4:00 PM | Varsity | Non-League | Normal | Home | Trumbull | Loss | 0-1 | | Treadwell Park - Newtown Treadwell Park | |
| MON 9/18 | 5:30 PM | Varsity | League | Normal | Away | New Milford | Win | 4-2 | | New Milford High School - Joe Wiser Stadium - NMHS | 2:45 PM - 1 Bus |
| WED 9/20 | 7:00 PM | Varsity | League | Normal | Away | Masuk | Win | 4-1 | | Masuk High School - Benedict Stadium Field @ Masuk HS | 4:15 PM - 1 Bus |
| SAT 9/23 | 10:00 AM | Varsity | League | Normal | Home | Branford | Win | 1-0 | | Newtown High School - Blue and Gold Stadium | |
| WED 9/27 | 5:00 PM | Varsity | League | Normal | Home | Brookfield | Win | 6-0 | | Treadwell Park - Newtown Treadwell Park | |
| SAT 9/30 | 10:00 AM | Varsity | Non-League | Normal | Home | Masuk | Win | 7-0 | | Newtown High School - Blue and Gold Stadium | |
| MON 10/2 | 5:30 PM | Varsity | League | Normal | Away | Weston | Loss | 0-2 | | Weston High School - WHS Lower Turf Field | 2:40 PM - 1 Bus |
| FRI 10/13 | 5:00 PM | Varsity | League | Normal | Home | New Fairfield | Win | 1-0 | | Newtown High School - Blue and Gold Stadium | |
| MON 10/16 | 7:00 PM | Varsity | League | Normal | Away | Joel Barlow | Loss | 1-2 | | Joel Barlow High School - Field I (Stadium) | |
| TUE 10/17 | 4:00 PM | Varsity | Non-League | Normal | Home | | Loss | 1-3 | | Newtown High School - Blue and Gold Stadium | |
| WED 10/18 | 6:00 PM | Varsity | League | Normal | Home | Bethel | Win | 7-0 | | Newtown High School - Blue and Gold Stadium | |
| FRI 10/20 | 4:00 PM | Varsity | League | Normal | Home | Immaculate | Win | 1-0 | | Treadwell Park - Newtown Treadwell Park | |
| TUE 10/24 | 7:00 PM | Varsity | League | Normal | Away | Pomperaug | Win | 3-0 | | Pomperaug High School - Stadium | 4:00 PM - 1 Bus |
| THU 10/26 | 6:00 PM | Varsity | Postseason | Normal | Home | Joel Barlow | Win | 4-1 | | Newtown High School - Blue and Gold Stadium | |
| MON 10/30 | 6:00 PM | Varsity | Postseason | Normal | Home | New Milford | Loss | 2-3 | | Newtown High School - Blue and Gold Stadium | |
| WED 11/8 | 2:00 PM | Varsity | Postseason | Normal | Away | Greenwich | Loss | 0-3 | | Greenwich High School - Cardinal Stadium | |