 | Cheshire Boys Basketball |
|
| Date | Opponent | H/A | Result |
| Wed., 12/12 | Career Magnet | Away | W 79-55 |
| Fri., 12/14 | West Haven | Away | L 64-66 |
| Tue., 12/18 | Xavier | Home | W 71-66 |
| Thu., 12/20 | Amity | Away | L 59-52 |
| Thu., 12/27 | Southington | Away | L 56-63 |
| Fri., 1/4 | Sheehan | Home | W 73-56 |
| Fri., 1/11 | Wilbur Cross | Away | L 54-61 |
| Tue., 1/15 | Shelton | Home | W 77-63 |
| Fri., 1/18 | Lyman Hall | Away | W 56-48 |
| Sat., 1/19 | Foran | Home | W 76-56 |
| Tue., 1/22 | Sheehan | Away | W 63-54 |
| Fri., 1/25 | Amity | Home | W 50-43 |
| Wed., 1/30 | Xavier | Away | L 47-65 |
| Fri., 2/1 | Shelton | Away | L 56-74 |
| Mon., 2/4 | Wilbur Cross | Home | L 59-68 |
| Wed., 2/6 | Wilby | Home | L 76-89 |
| Wed., 2/13 | Lyman Hall | Home | W 78-49 |
| Fri., 2/15 | Career Magnet | Home | L 62-64 |
| Tue., 2/19 | West Haven | Home | W 81-54 |
| Thu., 2/21 | Foran | Away | L 41-42 |
 Class LL State Tourney |
| Date | [Rd] Opponent | Site | Result |
| Mon., 3/4 | [1st] Simsbury | Simsbury | W 59-58 |
| Wed., 3/6 | [2nd] Bridg.Central | Bridg.Central | L 76-63 |