| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 12/19 | 1:00 p.m.and3:00pm | Varsity | League | Normal | Home | Bunnell | Loss | 53-87 | | Kaynor Tech Gymnasium | |
| MON 12/21 | 4:00 p.m.and6:00pm | Varsity | League | Normal | Home | CareerMagnet | Loss | 44-59 | | Kaynor Tech Gymnasium | |
| Trumbull | Loss | 35-68 |
| WED 12/30 | TBA | Varsity | League | Normal | Away | Stratford | Loss | 36-75 | | Needham Memorial Gymnasium | |
| TUE 1/5 | 7:00 p.m. | Varsity | League | Normal | Home | WaterburyCareer | Win | 60-55 | | Kaynor Tech Gymnasium | |
| THU 1/7 | 7:00 p.m. | Varsity | League | Normal | Away | CapitalPrep | Loss | 74-83 | | Capital Preparatory Magnet School | |
| MON 1/11 | 7:00 p.m. | Varsity | League | Normal | Home | JFKennedy | Loss | 41-68 | | Kaynor Tech Gymnasium | |
| WED 1/13 | 7:00 p.m. | Varsity | League | Normal | Home | PlattRVT | Win | 71-50 | | Kaynor Tech Gymnasium | |
| FRI 1/15 | 7:00 p.m. | Varsity | League | Normal | Home | HenryAbbottRVT | Loss | 60-73 | | Kaynor Tech Gymnasium | |
| TUE 1/19 | 7:00 p.m. | Varsity | League | Normal | Home | EliWhitneyRVT | Win | 79-70 | | Kaynor Tech Gymnasium | |
| FRI 1/22 | 7:00 p.m. | Varsity | League | Normal | Away | WarrenHarding | Loss | 50-99 | | Harding-Miska Gymnasium | |
| MON 1/25 | 7:00 p.m. | Varsity | League | Normal | Away | NorthHaven | Loss | 59-70 | | Fred Kelly Gymnasium | |
| FRI 1/29 | 7:00 p.m. | Varsity | League | Normal | Away | PlattRVT | Win | 55-51 | | Platt Tech baseball field | |
| WED 2/3 | 7:00 p.m. | Varsity | League | Normal | Home | OliverWolcottRVT | Win | 69-20 | | Kaynor Tech Gymnasium | |
| TUE 2/9 | 7:00 p.m. | Varsity | League | Normal | Away | Bassick | Loss | 45-85 | | Bassick Gymnasium | |
| FRI 2/12 | 7:00 p.m. | Varsity | League | Normal | Away | HolyCross | Loss | 40-64 | | Holy Cross HS | |
| TUE 2/16 | 1:30 p.m. | Varsity | League | Normal | Home | EmmettOBrienRVT | Win | 64-58 | | Kaynor Tech Gymnasium | |
| THU 2/18 | 6:00 p.m. | Varsity | League | Normal | Away | BullardHavensRVT | Win | 71-60 | | BHT GYM | |
| FRI 2/19 | 7:00 p.m. | Varsity | League | Normal | Away | Darien | Loss | 27-58 | | Darien High School | |
| MON 2/22 | 7:00 p.m. | Varsity | League | Normal | Home | ECGoodwinRVT | Win | 67-61 | | Kaynor Tech Gymnasium | |