| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 8/26 | 9:00 AM | Varsity | Scrimmage | Normal | Away | Bethel | | | | Immaculate High School - Mustang Valley | 7:30 AM |
| ATI | | |
| Lewis Mills | | |
| Masuk | | |
| New Fairfield | | |
| Seymour | | |
| Harding | | |
| THU 8/31 | 6:00 PM | Varsity | Scrimmage | Normal | Home | Seymour | | | | Weston High School - WHS Stadium Field | |
| FRI 9/8 | 7:00 PM | Varsity | Non-League | Normal | Home | Weaver | Win | 46-19 | | Weston High School - WHS Stadium Field | |
| SAT 9/9 | 10:00 AM | Junior Varsity | League | Normal | Home | Pomperaug | | | | Weston High School - WHS Stadium Field | |
| THU 9/14 | 7:30 PM | Varsity | League | Normal | Home | Notre Dame-Fairfield | Loss | 0-35 | | Weston High School - WHS Stadium Field | |
| SUN 9/17 | 12:00 PM | Junior Varsity | League | Normal | Away | Notre Dame-Fairfield | | | | Notre Dame - Fairfield - McCarty Stadium | 9:30 AM |
| SAT 9/23 | 1:00 PM | Varsity | Non-League | Normal | Away | Tolland | Loss | 7-36 | | Tolland High School - Stadium | 9:00 AM |
| FRI 9/29 | 7:00 PM | Varsity | League | Normal | Home | Bethel | Win | 21-7 | | Weston High School - WHS Stadium Field | |
| FRI 10/13 | 6:30 PM | Varsity | Non-League | Normal | Away | Pomperaug | Loss | 7-38 | | Pomperaug High School - Stadium | 3:30 PM |
| SAT 10/14 | Canceled | Junior Varsity | League | Canceled | Home | Pomperaug | | | | Weston High School - WHS Stadium Field | |
| FRI 10/20 | 7:00 PM | Varsity | Non-League | Normal | Away | Newtown | Loss | 7-42 | | Newtown High School - Blue and Gold Stadium | 3:30 PM |
| FRI 10/27 | 7:00 PM | Varsity | League | Normal | Home | New Fairfield | Loss | 7-33 | | Weston High School - WHS Stadium Field | |
| SAT 10/28 | Canceled | Junior Varsity | League | Canceled | Away | New Fairfield | | | | New Fairfield High School - Stadium Field | |
| FRI 11/3 | 7:00 PM | Varsity | League | Normal | Away | New Milford | Loss | 26-46 | | New Milford High School - Joe Wiser Stadium - NMHS | 3:30 PM |
| SAT 11/4 | Canceled | Junior Varsity | League | Canceled | Home | New Milford | | | | Weston High School - WHS Stadium Field | |
| FRI 11/10 | 7:00 PM | Varsity | League | Normal | Home | Brookfield | Loss | 28-50 | | Weston High School - WHS Stadium Field | |
| SAT 11/11 | Canceled | Junior Varsity | League | Canceled | Away | Brookfield | | | | Brookfield High School - BHS Back Turf | |
| FRI 11/17 | Canceled | Junior Varsity | League | Canceled | Home | Joel Barlow | | | | Weston High School - WHS Stadium Field | |
| MON 11/20 | Canceled | Junior Varsity | League | Canceled | Away | Bethel | | | | Bethel High School - DeSantis Field at Bethel High | 2:40 PM |
| THU 11/23 | 10:00 AM | Varsity | League | Normal | Away | Joel Barlow | Loss | 6-30 | | Joel Barlow High School - Field I (Stadium) | 7:30 AM |