| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 12/12 | 7:00 p.m. | Varsity | League | Normal | Away | Ridgefield | Loss | 33-60 | | RHS Main Gym | |
| FRI 12/14 | 5:30 p.m. | Varsity | League | Normal | Away | NewCanaan | Loss | 22-46 | | NCHS Gymnasium | |
| WED 12/19 | 5:30 p.m. | Varsity | League | Normal | Home | WarrenHarding | Win | 34-33 | | Westhill - Main Gymnasium | |
| FRI 12/21 | 6:00 p.m. | Varsity | League | Normal | Away | BridgeportCentral | Win | 62-27 | | Central H.S. Gym | |
| THU 12/27 | 4:00p.m/6:00 p.m. | Varsity | League | Normal | Away | Stamford | Loss | 34-46 | | Kuzco Gymnasium at Stamford High School | |
| SAT 12/29 | TBA | Varsity | League | Normal | Away | ScarsdaleNY | Loss | 22-35 | | Stamford High School Gym | |
| THU 1/3 | 6:00 p.m. | Varsity | League | Normal | Home | Wilton | Loss | 34-38 | | Westhill - Main Gymnasium | |
| MON 1/7 | 5:30 p.m. | Varsity | League | Normal | Home | Norwalk | Loss | 13-86 | | Westhill - Main Gymnasium | |
| THU 1/10 | 5:15 p.m. | Varsity | League | Normal | Away | Danbury | Loss | 39-51 | | Danbury High School - MAIN gym | |
| MON 1/14 | 5:30 p.m. | Varsity | League | Normal | Away | FairfieldWarde | Loss | 33-60 | | Fairfield Warde Large Gym | |
| THU 1/17 | 5:30 p.m. | Varsity | League | Normal | Home | TrinityCatholic | Loss | 33-46 | | Westhill - Main Gymnasium | |
| SAT 1/19 | 12:00 p.m. | Varsity | League | Normal | Away | Stamford | Loss | 17-49 | | Kuzco Gymnasium at Stamford High School | |
| TUE 1/22 | 5:30 p.m. | Varsity | League | Normal | Away | StJoseph | Loss | 28-60 | | St. Joseph High School | |
| FRI 1/25 | 7:00 p.m. | Varsity | League | Normal | Away | Trumbull | Loss | 39-61 | | THS Main Gym | |
| TUE 1/29 | 5:30 p.m. | Varsity | League | Normal | Home | Staples | Loss | 42-44 | | Westhill - Main Gymnasium | |
| FRI 2/1 | 5:30 p.m. | Varsity | League | Normal | Home | Greenwich | Loss | 47-54 | | Westhill - Main Gymnasium | |
| SAT 2/2 | 1:00 p.m. | Varsity | League | Normal | Home | Immaculate | Win | 51-46 | | Westhill - Main Gymnasium | |
| TUE 2/5 | 5:30 p.m. | Varsity | League | Normal | Away | BrienMcMahon | Win | 45-37 | | Brien McMahon HS | |
| FRI 2/8 | 5:30 p.m. | Varsity | League | Normal | Home | FairfieldLudlowe | Loss | 45-53 | | Westhill - Main Gymnasium | |
| WED 2/13 | 5:30 p.m. | Varsity | League | Normal | Home | Darien | Loss | 33-44 | | Westhill - Main Gymnasium | |