| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 12/13 | 5:45 p.m. | Varsity | League | Normal | Away | JosephForan | Loss | 20-43 | | Foran High School -Edna L. Fraser Gymnasium | |
| WED 12/15 | 5:30 p.m. | Varsity | League | Normal | Home | Wilton | Loss | 28-42 | | Weston High School-Gym (New) | |
| THU 1/6 | 7:00 p.m. | Varsity | League | Normal | Away | Pomperaug | Loss | 25-62 | | Pomperaug High School-Main Gym | |
| SAT 1/8 | 10:00 a.m. | Varsity | League | Normal | Away | NotreDameCatholic | Loss | Weston | | Notre Dame - Fairfield -Sister Marion Reilly Auditorium | |
| MON 1/10 | 6:00 p.m. | Varsity | League | Normal | Away | Bethel | Loss | 25-43 | | Bethel High School-BHS gym | |
| TUE 1/11 | 5:30 p.m. | Varsity | League | Normal | Away | NewMilford | Loss | Weston | | New Milford High School-Main Gym - NMHS | |
| THU 1/13 | 7:00 p.m. | Varsity | League | Normal | Away | NewFairfield | Loss | 21-36 | | New Fairfield High School-High School Gym | |
| SAT 1/15 | 10:00 a.m. | Varsity | League | Normal | Home | WarrenHarding | Win | 41-24 | | Weston High School-Gym (New) | |
| TUE 1/18 | 7:00 p.m. | Varsity | League | Normal | Home | Masuk | Loss | 39-49 | | Weston High School-Gym (New) | |
| FRI 1/21 | 7:00 p.m. | Varsity | League | Normal | Home | NewMilford | Win | 40-36 | | Weston High School-Gym (New) | |
| SAT 1/22 | 4:00 p.m. | Varsity | League | Normal | Home | BridgeportCentral | Win | 66-32 | | Weston High School-Gym (New) | |
| TUE 1/25 | 7:00 p.m. | Varsity | League | Normal | Away | Newtown | Loss | 20-24 | | Newtown High School-Gym | |
| FRI 1/28 | 5:15 p.m. | Varsity | League | Normal | Home | JoelBarlow | Win | 40-26 | | Weston High School-Gym (New) | |
| MON 1/31 | 6:00 p.m. | Varsity | League | Normal | Away | Bunnell | Win | 54-40 | | Bunnell HS-David Johnson Gymnasium | |
| THU 2/3 | 7:00 p.m. | Varsity | League | Normal | Home | Brookfield | Win | 45-24 | | Weston High School-Gym (New) | |
| SAT 2/5 | 4:00 p.m. | Varsity | League | Normal | Home | NewCanaan | Loss | 28-32 | | Weston High School-Gym (New) | |
| MON 2/7 | 7:00 p.m. | Varsity | League | Normal | Away | KolbeCathedral | Loss | 34-50 | | Cardinal Sheehan Center Bridgeport | |
| THU 2/10 | 7:00 p.m. | Varsity | League | Normal | Home | Stratford | Win | 41-30 | | Weston High School-Gym (New) | |
| SAT 2/12 | 12:00 p.m. | Varsity | League | Normal | Away | BrienMcMahon | Win | 56-34 | | Brien McMahon High School-Kehoe - King Gymnasium | |
| TUE 2/15 | 7:00 p.m. | Varsity | League | Normal | Home | Immaculate | Win | 45-39 | | Weston High School-Gym (New) | |
| MON 2/28 | 6:30 p.m. | Varsity | League | Normal | Away | Berlin | | | | Berlin High School-Gibney Gymnasium | |