| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 12/16 | 7:00 p.m. | Varsity | League | Normal | Home | EastHaven | Loss | 48-59 | | Kaynor Technical School-Kaynor Gymnasium | |
| TUE 12/20 | 7:00 p.m. | Varsity | League | Normal | Home | Masuk | Loss | 50-79 | | Kaynor Technical School-Kaynor Gymnasium | |
| THU 12/22 | 4:30 p.m. | Varsity | League | Normal | Away | JMWrightRVT | Win | 39-36 | | J M Wright Tech School-Thomas R. Good Gymnasium | |
| TUE 12/27 | 4:00 p.m. | Varsity | League | Normal | Away | HenryAbbottRVT | Loss | 35-64 | | Wilcox Tech-Gym | |
| THU 12/29 | 4:00 p.m. | Varsity | League | Normal | Away | HCWilcoxRVT | Loss | 54-58 | | Wilcox Tech-Gym | |
| TUE 1/3 | 4:00 p.m. | Varsity | League | Normal | Home | OliverWolcottRVT | Loss | 56-64 | | Kaynor Technical School-Kaynor Gymnasium | |
| FRI 1/6 | 7:00 p.m. | Varsity | League | Normal | Away | BullardHavensRVT | Loss | 41-54 | | Bullard Havens Tech-Gym | |
| MON 1/9 | 7:00 p.m. | Varsity | League | Normal | Away | Wilby | Loss | 51-81 | | Wilby High School-George Tirado Floor @ The Reggie O'Brien Gymnasium | |
| TUE 1/10 | 7:00 p.m. | Varsity | League | Normal | Home | WindhamRVT | Loss | 57-85 | | Kaynor Technical School-Kaynor Gymnasium | |
| THU 1/12 | 6:00 p.m. | Varsity | League | Normal | Home | WarrenHarding | Loss | 42-56 | | Kaynor Technical School-Kaynor Gymnasium | |
| TUE 1/17 | 7:00 p.m. | Varsity | League | Normal | Away | PlattRVT | Loss | 41-43 | | Platt Tech.-Gym | |
| WED 1/18 | 7:00 p.m. | Varsity | League | Normal | Home | Woodland | Loss | 71-79 | | Kaynor Technical School-Kaynor Gymnasium | |
| TUE 1/24 | 4:30 p.m. | Varsity | League | Normal | Away | OliverWolcottRVT | Loss | 50-51 | | Oliver Wolcott Technical High School-Gym | |
| THU 1/26 | 6:30 p.m. | Varsity | League | Normal | Away | EmmettOBrienRVT | Win | 56-43 | | Kaynor Technical School-Kaynor Gymnasium | |
| FRI 1/27 | 7:00 p.m. | Varsity | League | Normal | Home | BullardHavensRVT | Loss | 47-58 | | Kaynor Technical School-Kaynor Gymnasium | |
| TUE 1/31 | 5:30 p.m. | Varsity | League | Normal | Home | JMWrightRVT | Loss | 64-71 | | Kaynor Technical School-Kaynor Gymnasium | |
| TUE 2/7 | 7:00 p.m. | Varsity | League | Normal | Home | EliWhitneyRVT | Loss | 69-72 | | Kaynor Technical School-Kaynor Gymnasium | |
| WED 2/8 | 6:00 p.m. | Varsity | League | Normal | Away | HenryAbbottRVT | Loss | 35-71 | | Abbott V-T School-Daniel A. Garamella Memorial Gymnasium | |
| FRI 2/10 | 7:00 p.m. | Varsity | League | Normal | Home | HCWilcoxRVT | Win | 82-31 | | Kaynor Technical School-Kaynor Gymnasium | |
| TUE 2/14 | 7:00 p.m. | Varsity | League | Normal | Away | Watertown | Loss | 54-56 | | Watertown High-Robert B Cook Memorial Gym | |