| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 12/4 | 2:00 p.m. | Varsity | League | Normal | Home | NewFairfield | | | | Danbury High School-New Gym | |
| TUE 12/14 | 7:00 p.m. | Varsity | League | Normal | Away | SacredHeartAcademy | Loss | 83-48 | | Sacred Heart Academy-Gym | |
| THU 12/16 | 6:00 p.m. | Varsity | League | Normal | Away | WestHaven | Loss | 49-63 | | West Haven High School-Gym | |
| SAT 12/18 | 1:15 p.m. | Varsity | League | Normal | Away | Pomperaug | Win | 60-51 | | Pomperaug High School-Main Gym | |
| WED 12/22 | 6:00 p.m. | Varsity | League | Normal | Home | BridgeportCentral | Win | 75-15 | | Stamford High School-Kuczo Gymnasium | |
| TUE 12/28 | 6:00 p.m. | Varsity | League | Normal | Home | ClarkstownNorthNY | Win | 48-32 | | Stamford High School-Kuczo Gymnasium | |
| THU 12/30 | 6:00 p.m. | Varsity | League | Normal | Home | KolbeCathedral | Win | 57-34 | | Stamford High School-Kuczo Gymnasium | |
| TUE 1/4 | 6:00 p.m. | Varsity | League | Normal | Home | Ridgefield | Loss | 50-62 | | Stamford High School-Kuczo Gymnasium | |
| TUE 1/11 | 6:00 p.m. | Varsity | League | Normal | Home | BrienMcMahon | Win | 60-31 | | Stamford High School-Kuczo Gymnasium | |
| THU 1/13 | 6:00 p.m. | Varsity | League | Normal | Home | Danbury | Loss | 49-66 | | Stamford High School-Kuczo Gymnasium | |
| SAT 1/15 | 11:30 a.m. | Varsity | League | Normal | Home | Westhill | Win | 53-34 | | Stamford High School-Kuczo Gymnasium | |
| MON 1/17 | 5:30 p.m. | Varsity | League | Normal | Away | FairfieldWarde | Win | 54-26 | | Fairfield Warde HS-Large Gym | |
| MON 1/24 | 6:15 p.m. | Varsity | League | Normal | Away | NewCanaan | Win | 56-26 | | New Canaan High School-Main Gym | |
| TUE 1/25 | 6:00 p.m. | Varsity | League | Normal | Home | Wilton | Loss | 45-57 | | Stamford High School-Kuczo Gymnasium | |
| THU 1/27 | 6:30 p.m. | Varsity | League | Normal | Away | Greenwich | Loss | 48-47 | | Greenwich High School-Gymnasium | |
| MON 1/31 | 6:00 p.m. | Varsity | League | Normal | Away | StJoseph | Loss | 22-44 | | St. Joseph High School-Gym | |
| TUE 2/1 | 6:00 p.m. | Varsity | League | Normal | Home | Trumbull | Win | 59-41 | | Stamford High School-Kuczo Gymnasium | |
| TUE 2/8 | 7:00 p.m. | Varsity | League | Normal | Away | Staples | Win | 39-27 | | Staples High School-Staples Gym | |
| WED 2/9 | 7:00 p.m. | Varsity | League | Normal | Away | FairfieldLudlowe | Loss | 50-37 | | Fairfield Ludlowe High School-Main Gym | |
| MON 2/14 | 6:00 p.m. | Varsity | League | Normal | Home | Norwalk | Win | 38-35 | | Stamford High School-Kuczo Gymnasium | |
| WED 2/16 | 5:30 p.m. | Varsity | League | Normal | Away | Darien | Win | 49-36 | | Darien High School-DHS Main Gym | |