| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 12/21 | 12:00 p.m. | Varsity | League | Normal | Home | Hamden | Loss | 51-85 | | Greenwich High School-Gymnasium | |
| SAT 12/28 | 3:00 p.m. | Varsity | League | Normal | Away | SouthWindsor | Win | 40-38 | | Bristol Central Holiday Classic | |
| MON 12/30 | 7:30 p.m. | Varsity | League | Normal | Away | BristolCentral | Loss | 48-66 | | Bristol Central High School-Charles C. Marsh Gymnasium | |
| FRI 1/3 | 7:00 p.m. | Varsity | League | Normal | Home | Ridgefield | Loss | 45-64 | | Greenwich High School-Gymnasium | |
| TUE 1/7 | 7:00 p.m. | Varsity | League | Normal | Home | NewCanaan | Loss | 49-66 | | Greenwich High School-Gymnasium | |
| FRI 1/10 | 7:00 p.m. | Varsity | League | Normal | Away | Darien | Win | 79-73 | | Darien High School-DHS Main Gym | |
| TUE 1/14 | 7:00 p.m. | Varsity | League | Normal | Away | Stamford | Loss | 50-58 | | Stamford High School-Kuzco Gymnasium | |
| FRI 1/17 | 7:00 p.m. | Varsity | League | Normal | Home | StJoseph | Loss | 51-52 | | Greenwich High School-Gymnasium | |
| TUE 1/21 | 6:00 p.m. | Varsity | League | Normal | Away | BrienMcMahon | Loss | 57-73 | | Brien McMahon High School-Kehoe - King Gymnasium | |
| FRI 1/24 | 7:00 p.m. | Varsity | League | Normal | Away | Staples | Loss | 47-65 | | Staples High School-Staples Gym | |
| TUE 1/28 | 7:00 p.m. | Varsity | League | Normal | Home | Norwalk | Loss | 36-52 | | New Canaan High School-Main Gym | |
| THU 1/30 | 7:00 p.m. | Varsity | League | Normal | Away | FairfieldWarde | Loss | 23-61 | | Fairfield Warde HS-Large Gym | |
| MON 2/3 | 7:00 p.m. | Varsity | League | Normal | Away | Danbury | Win | 41-39 | | Danbury High School-Main Gym | |
| THU 2/6 | 7:00 p.m. | Varsity | League | Normal | Away | Westhill | Loss | 51-57 | | Westhill High School-Main Gym | |
| MON 2/10 | 7:00 p.m. | Varsity | League | Normal | Home | Wilton | Loss | 46-66 | | Greenwich High School-Gymnasium | |
| THU 2/13 | 7:00 p.m. | Varsity | League | Normal | Away | BridgeportCentral | Win | 58-40 | | Bridgeport Central High School-Barry McLeod Court | |
| WED 2/19 | 7:00 p.m. | Varsity | League | Normal | Home | Trumbull | Loss | 45-48 | | Greenwich High School-Gymnasium | |
| FRI 2/21 | 7:00 p.m. | Varsity | League | Normal | Away | RidgewoodNJ | Loss | 46-48 | | Ridgewood High School-Gym | |
| MON 2/24 | 7:00 p.m. | Varsity | League | Normal | Home | TrinityCatholic | Loss | 42-65 | | Greenwich High School-Gymnasium | |
| WED 2/26 | 7:00 p.m. | Varsity | League | Normal | Away | FairfieldLudlowe | Loss | 46-61 | | Fairfield Ludlowe High School-Main Gym | |