| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SUN 8/25 | 1:00 PM | Varsity | League | Normal | Home | Danbury | | | | New Milford High School - Joe Wiser Stadium - NMHS | |
| Hamden | | |
| Immaculate | | |
| Lakeview | | |
| Shepaug Valley | | |
| Watertown | | |
| TUE 8/27 | 4:00 PM | Varsity | Scrimmage | Normal | Home | Trumbull | | | | New Milford High School - Joe Wiser Stadium - NMHS | |
| SAT 8/31 | 9:00 AM | Varsity | League | Normal | Away | Trumbull | | | | New Fairfield High School - Marty Morgan Field | |
| Newtown | | |
| Shepaug Valley | | |
| Lakeview | | |
| Masuk | | |
| New Fairfield | | |
| Amity | | |
| Brookfield | | |
| TUE 9/3 | 5:30 PM | Varsity | Non-League | Normal | Home | Thomaston | Win | 5-0 | | New Milford High School - Joe Wiser Stadium - NMHS | |
| THU 9/5 | 5:30 PM | Varsity | Non-League | Normal | Home | Pomperaug | Loss | 0-1 | | New Milford High School - Joe Wiser Stadium - NMHS | |
| WED 9/11 | 5:30 PM | Varsity | League | Normal | Home | Masuk | Win | 3-0 | | New Milford High School - Joe Wiser Stadium - NMHS | |
| THU 9/12 | 5:30 PM | Varsity | Non-League | Normal | Home | Watertown | Win | 3-0 | | New Milford High School - Joe Wiser Stadium - NMHS | |
| SAT 9/14 | 12:30 PM | Varsity | Non-League | Normal | Away | Amity | Loss | 1-3 | | Amity Regional High School - William Johnson Stadium Field | 10:30 AM |
| MON 9/16 | 5:30 PM | Varsity | League | Normal | Home | New Fairfield | Win | 2-1 | | New Milford High School - Joe Wiser Stadium - NMHS | |
| WED 9/18 | 5:30 PM | Varsity | League | Normal | Home | Bethel | Win | 4-0 | | New Milford High School - Joe Wiser Stadium - NMHS | |
| FRI 9/20 | 5:30 PM | Varsity | Non-League | Normal | Home | Lakeview | | | | New Milford High School - Joe Wiser Stadium - NMHS | |
| MON 9/23 | 5:30 PM | Varsity | League | Normal | Away | Newtown | | | | Newtown High School - Blue and Gold Stadium | 2:30 PM |
| WED 9/25 | 7:15 PM | Varsity | League | Normal | Away | Pomperaug | | | | Pomperaug High School - Stadium | 4:15 PM |
| MON 9/30 | 5:30 PM | Varsity | League | Normal | Home | Weston | | | | New Milford High School - Joe Wiser Stadium - NMHS | |
| WED 10/2 | 4:30 PM | Varsity | Non-League | Normal | Away | Ridgefield | | | | Ridgefield High School - Tiger Hollow Stadium | 3:00 PM |
| SAT 10/5 | 10:00 AM | Varsity | League | Normal | Away | Masuk | | | | Masuk High School - Benedict Stadium Field @ Masuk HS | 8:30 AM |
| MON 10/7 | 5:30 PM | Varsity | League | Normal | Away | Brookfield | | | | Brookfield High School - BHS Stadium Field | 2:45 PM |
| WED 10/9 | 5:30 PM | Varsity | League | Normal | Home | Immaculate | | | | New Milford High School - Joe Wiser Stadium - NMHS | |
| WED 10/16 | 7:00 PM | Varsity | League | Normal | Away | Joel Barlow | | | | Joel Barlow High School - Field I (Stadium) | 3:45 PM |