| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 12/23 | 5:00 p.m. | Varsity | League | Normal | Away | Wilton | Loss | 48-78 | | | |
| THU 12/29 | 7:30 p.m. | Varsity | League | Normal | Away | Stratford | Win | 62-57 | | Needham Memorial Gymnasium | |
| FRI 12/30 | TBA | Varsity | League | Normal | Away | Trumbull | Loss | 46-52 | | | |
| TUE 1/3 | 7:00 p.m. | Varsity | League | Normal | Home | BridgeportCentral | Win | 73-56 | | Westhill - Main Gymnasium | |
| FRI 1/6 | 7:00 p.m. | Varsity | League | Normal | Home | JoelBarlow | Win | 47-38 | | Westhill - Main Gymnasium | |
| TUE 1/10 | 7:00 p.m. | Varsity | League | Normal | Away | Norwalk | Loss | 55-56(OT) | | Norwalk High Gym | |
| FRI 1/13 | 7:00 p.m. | Varsity | League | Normal | Home | Danbury | Loss | 39-46 | | Westhill - Main Gymnasium | |
| TUE 1/17 | 7:00 p.m. | Varsity | League | Normal | Home | FairfieldWarde | Loss | 76-95 | | Westhill - Main Gymnasium | |
| FRI 1/20 | 7:00 p.m. | Varsity | League | Normal | Away | TrinityCatholic | Loss | 54-62 | | Walsh Court | |
| TUE 1/24 | 7:00 p.m. | Varsity | League | Normal | Home | StJoseph | Win | 55-42 | | Westhill - Main Gymnasium | |
| FRI 1/27 | 7:00 p.m. | Varsity | League | Normal | Home | Trumbull | Loss | 46-64 | | Westhill - Main Gymnasium | |
| WED 2/1 | 7:00 p.m. | Varsity | League | Normal | Away | Staples | Loss | 54-57 | | Staples H.S. Gym | |
| FRI 2/3 | 7:00 p.m. | Varsity | League | Normal | Away | Greenwich | Win | 65-60 | | GHS Gymnasium | |
| TUE 2/7 | 7:00 p.m. | Varsity | League | Normal | Away | FairfieldLudlowe | Win | 56-48 | | FLHS Main Gym | |
| WED 2/8 | 6:30 p.m. | Varsity | League | Normal | Away | AIPrinceRVT | Loss | 64-69 | | Prince Tech | |
| FRI 2/10 | 7:00 p.m. | Varsity | League | Normal | Home | BrienMcMahon | Loss | 66-68 | | Westhill - Main Gymnasium | |
| MON 2/13 | 7:00 p.m. | Varsity | League | Normal | Home | Ridgefield | Loss | 46-60 | | Westhill - Main Gymnasium | |
| WED 2/15 | 7:00 p.m. | Varsity | League | Normal | Away | Darien | Loss | 42-59 | | DHS Main Gym | |
| MON 2/20 | 7:00 p.m. | Varsity | League | Normal | Away | Stamford | Loss | 60-65 | | Stamford High School | |
| WED 2/22 | 7:00 p.m. | Varsity | League | Normal | Home | NewCanaan | Loss | 62-57 | | Westhill - Main Gymnasium | |