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Winchester Varsity Boys Basketball Schedule
| Date | Opponent | Result | W-L (League) | Type | Location | Tickets | Live Stream |
|---|---|---|---|---|---|---|---|
| 0-0 (0-0) | Scrimmage | Winchester, MA | - | - | |||
| 0-0 (0-0) | Scrimmage | Concord, MA | - | - | |||
| W 72-30 | 1-0 (1-0) | League | Winchester, MA | - | - | ||
| L 64-66 | 1-1 (1-1) | League | Arlington, MA | - | - | ||
| W 84-49 | 2-1 (2-1) | League | Acton, MA | - | - | ||
| W 64-60 | 3-1 (2-1) | Tournament | Winchester, MA | - | - | ||
| W 66-41 | 4-1 (2-1) | Tournament | Winchester, MA | - | - | ||
| W 68-42 | 5-1 (3-1) | League | Winchester, MA | - | - | ||
| W 75-48 | 6-1 (4-1) | League | Winchester, MA | - | - | ||
| W 67-64 | 7-1 (5-1) | League | Lexington, MA | - | - | ||
| W 75-52 | 8-1 (6-1) | League | Wakefield, MA | - | - | ||
| W 71-56 | 9-1 (7-1) | League | Reading, MA | - | - | ||
| W 87-62 | 10-1 (8-1) | League | Winchester, MA | - | - | ||
| W 55-45 | 11-1 (9-1) | League | Burlington, MA | - | - | ||
| W 75-41 | 12-1 (10-1) | League | Winchester, MA | - | - | ||
| W 63-55 | 13-1 (11-1) | League | Winchester, MA | - | - | ||
| W 75-47 | 14-1 (12-1) | League | Woburn, MA | - | - | ||
| L 66-69 | 14-2 (12-2) | League | Winchester, MA | - | - | ||
| W 85-63 | 15-2 (13-2) | League | Winchester, MA | - | - | ||
| W 55-52 | 16-2 (14-2) | League | Belmont, MA | - | - | ||
| L 38-45 | 16-3 (14-2) | Tournament | North Andover, MA | - | Watch | ||
| 16-3 (14-2) | Tournament | Newtonville, MA | - | - |