| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2024 | (5) Winchester Red & Black at (0) Wilmington Wildcats | Breakaway Ice Center |
| December 18, 2024 | (5) Winchester Red & Black at (2) Stoneham Spartans | Stoneham Arena |
| December 21, 2024 | (1) Melrose Red Hawks at (5) Winchester Red & Black | O'Brien Arena |
| December 23, 2024 | (4) St. Mary's Lynn Spartans at (3) Winchester Red & Black | O'Brien Arena |
| December 28, 2024 | (4) Winchester Red & Black at (2) Reading Rockets | Burbank Ice Arena |
| December 31, 2024 | (0) Malden Catholic Lancers at (3) Winchester Red & Black | O'Brien Arena |
| January 04, 2025 | (4) Belmont Marauders at (1) Winchester Red & Black | O'Brien Arena |
| January 08, 2025 | (2) Winchester Red & Black at (3) Arlington Spy Ponders
Arlington wins in OT |
Ed Burns Arena |
| January 11, 2025 | (1) Winchester Red & Black at (3) Woburn Tanners | O'Brien Arena |
| January 13, 2025 | (5) Hingham Harbormen at (3) Winchester Red & Black | O'Brien Arena |
| January 18, 2025 | (3) Reading Rockets at (0) Winchester Red & Black | O'Brien Arena |
| January 22, 2025 | (1) Wakefield Warriors at (7) Winchester Red & Black | O'Brien Arena |
| January 24, 2025 | (3) Watertown/Wayland Raiders at (6) Winchester Red & Black | O'Brien Arena |
| January 26, 2025 | (3) Winchester Red & Black at (5) Hingham Harbormen
Ed Burns Tournament |
Ed Burns Arena |
| January 29, 2025 | (0) Burlington Red Devils at (2) Winchester Red & Black | O'Brien Arena |
| January 31, 2025 | (1) Winchester Red & Black at (3) Belmont Marauders | John A. Ryan Arena |
| February 02, 2025 | (1) Concord-Carlisle Patriots at (4) Winchester Red & Black
Ed Burns Coffee Pot Tournament - Doherty Consolation |
Chelmsford Forum |
| February 05, 2025 | (6) Arlington Spy Ponders at (1) Winchester Red & Black | O'Brien Arena |
| February 07, 2025 | (2) Woburn Tanners at (2) Winchester Red & Black
Winchester wins in OT |
O'Brien Arena |
| February 12, 2025 | (4) Pope Francis Cardinals at (1) Winchester Red & Black | O'Brien Arena |
| February 17, 2025 | (5) Winchester Red & Black at (3) Tewksbury Redmen
Ed Burns Classic Coffe Pot - Doherty Consolation - RE-SCHEDULED FROM 2-9-24 |
John A. Ryan Arena |
| February 19, 2025 | (3) Catholic Memorial Knights at (2) Winchester Red & Black
CM wins in OT |
O'Brien Arena |
| February 25, 2025 | (1) Shrewsbury Colonials at (4) Winchester Red & Black
MIAA D1 BOYS STATE TOURNAMENT - Round 32 |
O'Brien Arena |
| March 02, 2025 | (2) Winchester Red & Black at (1) Belmont Marauders
MIAA D1 Boys State Tournament - Round of 16 - Winchester Win 3OT |
John A. Ryan Arena |
| March 06, 2025 | (4) Saint John's Shrewsbury Pioneers at (3) Winchester Red & Black
MIAA D1 BOYS STATE TOURNAMENT - Round 8 (SJS WINS IN OT) |
Chelmsford Forum |
