| Date & Time | Game | Venue |
|---|---|---|
| December 13, 2025 | (2) Stoneham Spartans at (3) Winchester Red & Black
Winchester Win in OT |
O'Brien Arena |
| December 17, 2025 | (2) Winchester Red & Black at (0) Melrose Red Hawks | Kasabuski Arena |
| December 20, 2025 | (3) Winchester Red & Black at (2) Wakefield Warriors
Winchester wins in OT |
Stoneham Arena |
| December 23, 2025 | (2) Xaverian Hawks at (1) Winchester Red & Black | O'Brien Arena |
| January 03, 2026 | (1) Arlington Spy Ponders at (2) Winchester Red & Black | O'Brien Arena |
| January 07, 2026 | (2) Woburn Tanners at (1) Winchester Red & Black | O'Brien Arena |
| January 10, 2026 | (1) Winchester Red & Black at (7) Hingham Harbormen | Pilgrim Arena |
| January 14, 2026 | (1) Winchester Red & Black at (2) Reading Rockets | Burbank Ice Arena |
| January 17, 2026 | (3) Winchester Red & Black at (1) Belmont Marauders | Skip Viglirolo Rink |
| January 21, 2026 | (3) Winchester Red & Black at (2) Watertown/Wayland Raiders | John A. Ryan Arena |
| January 24, 2026 | (1) Winchester Red & Black at (4) Burlington Red Devils | Burlington Ice Palace |
| January 25, 2026 | (0) Franklin Panthers at (6) Winchester Red & Black
Ed Burns Tournament |
Canton Ice House |
| January 28, 2026 | (0) Wilmington Wildcats at (9) Winchester Red & Black | O'Brien Arena |
| January 31, 2026 | (1) Winchester Red & Black at (5) Arlington Spy Ponders | Ed Burns Arena |
| February 01, 2026 | (0) Walpole Timberwolves at (2) Winchester Red & Black
Ed Burns Tournament |
Cadillac Ice Arena |
| February 04, 2026 | (3) Winchester Red & Black at (3) Woburn Tanners | O'Brien Arena |
| Feb. 7 Postponed | Winchester Red & Black at St. Mary's Lynn Spartans | Connery Memorial Arena |
| February 08, 2026 | (1) Woburn Tanners at (2) Winchester Red & Black
Ed Burns Tournament - Championship |
O'Brien Arena |
| February 11, 2026 | (3) Reading Rockets at (0) Winchester Red & Black | O'Brien Arena |
| February 14, 2026 | (1) Belmont Marauders at (6) Winchester Red & Black | O'Brien Arena |
| February 16, 2026 | (3) Winchester Red & Black at (3) Malden Catholic Lancers | Valley Forum II |
| February 18, 2026 | (0) Winchester Red & Black at (3) Catholic Memorial Knights | Warrior Ice Arena |
| February 19, 2026 | (1) Winchester Red & Black at (2) St. Mary's Lynn Spartans | Connery Memorial Arena |
| February 25, 2026 | (5) Winchester Red & Black at (4) Wachusett Mountaineers
MIAA D1 - Boys State Tournament - Round 32 |
NorthStar Ice Sports |
| February 28, 2026 | (2) Winchester Red & Black at (5) Catholic Memorial Knights
MIAA D1 - Boys State Tournament - Round 16 |
Warrior Ice Arena |
