| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 12/20 | 4:00 p.m. | Varsity | League | Normal | Home | Simsbury | Loss | 51-52 | | Lower Gym | |
| MON 12/22 | 7:00 p.m. | Varsity | League | Normal | Away | Pomperaug | Win | 61-55 | | PHS Main Gym | |
| SAT 12/27 | 6:00 p.m. | Varsity | League | Normal | Away | BrienMcMahon | Loss | 55-61 | | | |
| Weston | Loss | 48-58 |
| SAT 1/3 | 2:00 p.m. | Varsity | League | Normal | Away | Danbury | Win | 59-53 | | Danbury High School - MAIN gym | |
| TUE 1/6 | 7:00 p.m. | Varsity | League | Normal | Home | NewMilford | Win | 69-59 | | Lower Gym | |
| SAT 1/10 | 6:00 p.m. | Varsity | League | Normal | Home | Westhill | Loss | 59-71 | | Lower Gym | |
| TUE 1/13 | 5:15 p.m. | Varsity | League | Normal | Home | NewFairfield | Win | 50-45 | | Lower Gym | |
| FRI 1/16 | 7:00 p.m. | Varsity | League | Normal | Away | Weston | Loss | 56-58 | | WHS Gymnasium | |
| TUE 1/20 | 7:00 p.m. | Varsity | League | Normal | Home | Brookfield | Win | 54-44 | | Lower Gym | |
| FRI 1/23 | 7:00 p.m. | Varsity | League | Normal | Away | NotreDameCatholic | Loss | 45-57 | | Sister Marion Rielly Auditorium at Notre Dame | |
| WED 1/28 | 7:00 p.m. | Varsity | League | Normal | Home | KolbeCathedral | Win | 71-64 | | Lower Gym | |
| FRI 1/30 | 7:00 p.m. | Varsity | League | Normal | Home | Pomperaug | Loss | 35-58 | | Lower Gym | |
| TUE 2/3 | 7:00 p.m. | Varsity | League | Normal | Away | Newtown | Loss | 61-69 | | Newtown High School Gymnasium | |
| FRI 2/6 | 7:00 p.m. | Varsity | League | Normal | Away | Masuk | Win | 62-54 | | David Strong Gymnasium @ Masuk High School | |
| TUE 2/10 | 7:00 p.m. | Varsity | League | Normal | Home | Bethel | Win | 64-38 | | Lower Gym | |
| FRI 2/13 | 7:00 p.m. | Varsity | League | Normal | Away | Stratford | Win | 55-43 | | Needham Memorial Gymnasium | |
| TUE 2/17 | 7:00 p.m. | Varsity | League | Normal | Away | Immaculate | Win | 64-43 | | Immaculate High School | |
| FRI 2/20 | 7:00 p.m. | Varsity | League | Normal | Home | Bunnell | Loss | 45-57 | | Lower Gym | |
| TUE 2/24 | 7:00 p.m. | Varsity | League | Normal | Away | NewMilford | Win | 64-50 | | New Milford High School | |