| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 12/11 | 7:00 p.m. | Varsity | League | Normal | Away | Masuk | Loss | 34-53 | | David Strong Gymnasium @ Masuk High School | |
| THU 12/13 | 5:15 p.m. | Varsity | League | Normal | Away | Seymour | Loss | 42-59 | | Masuk High School | |
| MON 12/17 | 4:00 p.m. | Varsity | League | Normal | Home | BullardHavensRVT | Win | 47-44 | | Bassick Gymnasium | |
| FRI 12/21 | 4:00 p.m. | Varsity | League | Normal | Home | FairfieldWarde | Loss | 30-56 | | Bassick Gymnasium | |
| THU 12/27 | 1:00 p.m. | Varsity | League | Normal | Away | WarrenHarding | Win | 59-31 | | Harding-Miska Gymnasium | |
| FRI 12/28 | 1:00 p.m. | Varsity | League | Normal | Away | TrinityCatholic | Loss | 44-56 | | Harding High School | |
| WED 1/2 | 6:00 p.m. | Varsity | League | Normal | Away | CareerMagnet | Loss | 37-53 | | Career High School | |
| FRI 1/4 | 5:00 p.m. | Varsity | League | Normal | Home | BrienMcMahon | Win | 60-50 | | Bassick Gymnasium | |
| TUE 1/8 | 4:30 p.m. | Varsity | League | Normal | Home | CapitalPrep | Loss | 34-62 | | Bassick Gymnasium | |
| THU 1/10 | 5:30 p.m. | Varsity | League | Normal | Away | Wilton | Loss | 35-38 | | Nicholas Zeoli Field House | |
| SAT 1/12 | 11:00 a.m. | Varsity | League | Normal | Away | Norwalk | Loss | 31-84 | | Scarso Gymnasium | |
| TUE 1/15 | 6:00 p.m. | Varsity | League | Normal | Away | CapitalPrep | Loss | 20-54 | | Capital Preparatory Magnet School | |
| THU 1/17 | 5:30 p.m. | Varsity | League | Normal | Away | FairfieldLudlowe | Loss | 46-65 | | FLHS Main Gym | |
| SAT 1/19 | 3:00 p.m. | Varsity | League | Normal | Away | EastHaven | Loss | 43-82 | | East Haven High School | |
| MON 1/21 | 4:00 p.m. | Varsity | League | Normal | Away | NotreDameCatholic | Loss | 43-80 | | Sister Marion Rielly Auditorium at Notre Dame | |
| FRI 1/25 | 4:00 p.m. | Varsity | League | Normal | Home | BridgeportCentral | Win | 91-32 | | Bassick Gymnasium | |
| MON 2/4 | 6:00 p.m. | Varsity | League | Normal | Away | JonathanLaw | Loss | 62-64 | | Jonathan Law HS-Richetelli Gymnasium | |
| SAT 2/9 | 11:00 a.m. | Varsity | League | Normal | Away | BrienMcMahon | Win | 58-46 | | Brien McMahon HS | |
| WED 2/13 | 4:00 p.m. | Varsity | League | Normal | Away | Staples | Win | 54-51 | | Staples H.S. Gym | |
| THU 2/14 | 5:00 p.m. | Varsity | League | Normal | Home | WarrenHarding | Win | 66-45 | | Bassick Gymnasium | |