| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 12/16 | 5:00 p.m. | Varsity | League | Normal | Away | Darien | Loss | 37-55 | | Darien High School-DHS Main Gym | |
| WED 12/18 | 4:30 p.m. | Varsity | League | Normal | Home | CapitalPrep | Loss | 39-50 | | Bassick High School-Gym | |
| FRI 12/20 | 4:30 p.m. | Varsity | League | Normal | Home | NewFairfield | Win | 52-45 | | Bassick High School-Gym | |
| FRI 12/27 | 11:00 a.m. | Varsity | League | Normal | Away | BridgeportCentral | Win | 92-38 | | Bridgeport Central High School-Barry McLeod Court | |
| SAT 12/28 | TBA | Varsity | League | Normal | Away | TrinityCatholic | Win | 72-62 | | Bassick High School-Gym | |
| MON 12/30 | 4:30 p.m. | Varsity | League | Normal | Away | CapitalPrep | Win | 48-41 | | Capital Preparatory Magnet 2-Gym | |
| TUE 1/7 | 5:00 p.m. | Varsity | League | Normal | Away | FairfieldWarde | Loss | 58-62 | | Fairfield Warde HS-Large Gym | |
| FRI 1/10 | 6:00 p.m. | Varsity | League | Normal | Away | Masuk | Win | 62-38 | | Masuk High School-David Strong Gymnasium @ Masuk HS | |
| MON 1/13 | 4:30 p.m. | Varsity | League | Normal | Home | Wilton | Win | 56-42 | | Bassick High School-Gym | |
| WED 1/15 | 3:45 p.m. | Varsity | League | Normal | Away | EliWhitneyRVT | Win | 99-29 | | Eli Whitney RVTS-Gym | |
| FRI 1/17 | 4:30 p.m. | Varsity | League | Normal | Home | JoelBarlow | Win | 56-39 | | Bassick High School-Gym | |
| THU 1/23 | 4:30 p.m. | Varsity | League | Normal | Home | FairfieldLudlowe | Loss | 60-67 | | Bassick High School-Gym | |
| SAT 1/25 | 5:00 p.m. | Varsity | League | Normal | Away | Weston | Win | 61-53 | | Weston High School-Gym (New) | |
| WED 1/29 | 4:30 p.m. | Varsity | League | Normal | Away | BullardHavensRVT | Win | 65-48 | | Bullard Havens Tech-Gym | |
| SAT 2/1 | 12:00 p.m. | Varsity | League | Normal | Away | StJoseph | Loss | 51-52 | | St. Joseph High School-Gym | |
| MON 2/3 | 5:30 p.m. | Varsity | League | Normal | Home | Staples | Loss | 55-73 | | Bassick High School-Gym | |
| WED 2/5 | 7:00 p.m. | Varsity | League | Normal | Away | KolbeCathedral | Loss | 45-53 | | Kolbe-cathedral High School-Cardinal Shehan Center | |
| MON 2/10 | 4:30 p.m. | Varsity | League | Normal | Home | JonathanLaw | Win | 51-46 | | Bassick High School-Gym | |
| THU 2/13 | 5:30 p.m. | Varsity | League | Normal | Home | NewCanaan | Loss | 42-51 | | Bassick High School-Gym | |
| TUE 2/25 | 5:30 p.m. | Varsity | League | Normal | Away | WarrenHarding | Win | 86-37 | | Warren Harding High School-Gym | |