| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 12/17 | 12:30 p.m. | Varsity | League | Normal | Away | Brookfield | Loss | 45-66 | | Brookfield High School-BHS Big Gym | |
| TUE 12/20 | 7:00 p.m. | Varsity | League | Normal | Away | JFKennedy | Loss | 50-71 | | John F. Kennedy High School-Jack Taglia Gymnasium | |
| THU 12/22 | 6:30 p.m. | Varsity | League | Normal | Home | Woodland | Win | 67-51 | | Wolcott High School-Main Gym | |
| TUE 12/27 | 6:00 p.m. | Varsity | League | Normal | Away | WaterburyCareer | Loss | 66-75 | | Waterbury Career Academy-Gymnasium | |
| TUE 1/3 | 7:00 p.m. | Varsity | League | Normal | Home | HolyCross | Loss | 54-71 | | Wolcott High School-Main Gym | |
| FRI 1/6 | 6:00 p.m. | Varsity | League | Normal | Away | Ansonia | Win | 51-44 | | Ansonia High School-Gym | |
| TUE 1/10 | 7:30 p.m. | Varsity | League | Normal | Home | Oxford | Win | 54-45 | | Wolcott High School-Main Gym | |
| FRI 1/13 | 7:00 p.m. | Varsity | League | Normal | Away | Watertown | Win | 57-44 | | Watertown High-Robert B Cook Memorial Gym | |
| TUE 1/17 | 7:00 p.m. | Varsity | League | Normal | Away | Naugatuck | Loss | 61-64 | | Naugatuck High School-Edward Mariano Gymnasium | |
| FRI 1/20 | 7:00 p.m. | Varsity | League | Normal | Home | Wilby | Loss | 61-84 | | Wolcott High School-Main Gym | |
| TUE 1/24 | 7:00 p.m. | Varsity | League | Normal | Home | Torrington | Loss | 48-75 | | Wolcott High School-Main Gym | |
| FRI 1/27 | 7:00 p.m. | Varsity | League | Normal | Away | Derby | Win | 76-45 | | Derby High School-DHS Vitello Gym | |
| TUE 1/31 | 7:00 p.m. | Varsity | League | Normal | Home | Watertown | Win | 55-51 | | Wolcott High School-Main Gym | |
| SAT 2/4 | 2:00 p.m. | Varsity | League | Normal | Home | NewFairfield | Win | 55-51 | | Wolcott High School-Main Gym | |
| TUE 2/7 | 7:00 p.m. | Varsity | League | Normal | Home | Naugatuck | Win | 56-44 | | Wolcott High School-Main Gym | |
| FRI 2/10 | 7:00 p.m. | Varsity | League | Normal | Away | Torrington | Loss | 44-50 | | Torrington High School-Connie Donahue Gymnasium | |
| MON 2/13 | 7:00 p.m. | Varsity | League | Normal | Home | StPaulCatholic | Win | 69-52 | | Wolcott High School-Main Gym | |
| WED 2/15 | 7:15 p.m. | Varsity | League | Normal | Away | StPaulCatholic | Loss | 30-47 | | St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium | |
| FRI 2/17 | 7:00 p.m. | Varsity | League | Normal | Home | Crosby | Loss | 57-83 | | Wolcott High School-Main Gym | |
| TUE 2/21 | 7:00 p.m. | Varsity | League | Normal | Away | Seymour | Loss | 54-63 | | Seymour High School-Gym | |