| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 12/16 | 7:00 p.m. | Varsity | League | Normal | Away | JoelBarlow | Loss | 35-45 | | Joel Barlow High School-Lower Gym | |
| TUE 12/20 | 7:00 p.m. | Varsity | League | Normal | Away | Darien | Loss | 35-77 | | Darien High School-DHS Main Gym | |
| TUE 12/27 | 6:00 p.m. | Varsity | League | Normal | Home | Bethel | Loss | 43-47 | | Westhill High School-Main Gym | |
| THU 12/29 | 4:00 p.m. | Varsity | League | Normal | Home | BridgeportCentral | Loss | 38-65 | | Westhill High School-Main Gym | |
| THU 1/5 | 7:00 p.m. | Varsity | League | Normal | Away | Trumbull | Loss | 41-64 | | Trumbull High School-THS Main Gym | |
| TUE 1/10 | 7:00 p.m. | Varsity | League | Normal | Home | Darien | Loss | 48-62 | | Westhill High School-Main Gym | |
| THU 1/12 | 7:00 p.m. | Varsity | League | Normal | Away | BrienMcMahon | Loss | 46-72 | | Brien McMahon High School-Kehoe - King Gymnasium | |
| SAT 1/14 | 3:00 p.m. | Varsity | League | Normal | Away | Stamford | Loss | 38-70 | | Stamford High School-Kuczo Gymnasium | |
| MON 1/16 | 1:30 p.m. | Varsity | League | Normal | Home | BridgeportCentral | Loss | 50-63 | | Westhill High School-Main Gym | |
| WED 1/18 | 7:00 p.m. | Varsity | League | Normal | Home | EastLyme | Loss | 49-77 | | Westhill High School-Main Gym | |
| FRI 1/20 | 7:00 p.m. | Varsity | League | Normal | Home | FairfieldLudlowe | Loss | 41-47 | | Westhill High School-Main Gym | |
| TUE 1/24 | 7:00 p.m. | Varsity | League | Normal | Away | Staples | Loss | 60-41 | | Staples High School-Staples Gym | |
| FRI 1/27 | 7:00 p.m. | Varsity | League | Normal | Home | NewCanaan | Loss | 72-26 | | Westhill High School-Main Gym | |
| TUE 1/31 | 7:00 p.m. | Varsity | League | Normal | Away | Norwalk | Loss | 67-45 | | Norwalk High School-Tom Scarso Gymnasium | |
| THU 2/2 | 7:00 p.m. | Varsity | League | Normal | Away | Ridgefield | Loss | 88-29 | | Ridgefield High School-Main Gym | |
| TUE 2/7 | 7:00 p.m. | Varsity | League | Normal | Away | Wilton | Loss | 76-51 | | Wilton High School-Nicholas Zeoli Field House | |
| MON 2/13 | 7:00 p.m. | Varsity | League | Normal | Home | StJoseph | Loss | 66-80 | | Westhill High School-Main Gym | |
| WED 2/15 | 7:00 p.m. | Varsity | League | Normal | Home | Danbury | Loss | 41-84 | | Westhill High School-Main Gym | |
| MON 2/20 | 7:00 p.m. | Varsity | League | Normal | Away | Greenwich | Loss | 34-61 | | Greenwich High School-Gymnasium | |
| WED 2/22 | 7:00 p.m. | Varsity | League | Normal | Home | FairfieldWarde | Loss | 55-68 | | Westhill High School-Main Gym | |