| Date & Time | Game | Venue |
|---|---|---|
| December 16, 2024 | (1) Longmeadow Lancers at (2) Winchester Red & Black | O'Brien Arena |
| December 18, 2024 | (7) Winchester Red & Black at (1) Stoneham/Wilmington Spartans | Stoneham Arena |
| December 21, 2024 | (3) Melrose Red Hawks at (2) Winchester Red & Black | O'Brien Arena |
| December 28, 2024 | (3) Andover Golden Warriors at (3) Winchester Red & Black | O'Brien Arena |
| December 30, 2024 | (3) Winchester Red & Black at (4) Tewksbury/Methuen Red Rangers | Methuen High School Rink |
| January 04, 2025 | (0) Belmont/Watertown Marauders at (0) Winchester Red & Black | O'Brien Arena |
| January 08, 2025 | (2) Winchester Red & Black at (1) Arlington Spy Ponders | Ed Burns Arena |
| January 11, 2025 | (0) Winchester Red & Black at (1) Woburn Tanners | O'Brien Arena |
| January 15, 2025 | (4) Winchester Red & Black at (0) Lexington Minutemen | Hayden Ice Facility |
| January 18, 2025 | (3) Reading Rockets at (2) Winchester Red & Black | O'Brien Arena |
| January 20, 2025 | (1) Winchester Red & Black at (3) St. Mary's Lynn Spartans | Connery Memorial Arena |
| January 22, 2025 | (1) Wakefield Warriors at (5) Winchester Red & Black | O'Brien Arena |
| January 25, 2025 | (3) Winthrop Vikings at (2) Winchester Red & Black
Winthrop wins in OT |
O'Brien Arena |
| January 29, 2025 | (1) Burlington Red Devils at (3) Winchester Red & Black | O'Brien Arena |
| February 01, 2025 | (2) Winchester Red & Black at (3) Belmont/Watertown Marauders | John A. Ryan Arena |
| February 05, 2025 | (4) Arlington Spy Ponders at (0) Winchester Red & Black | O'Brien Arena |
| February 08, 2025 | (1) Winchester Red & Black at (2) Woburn Tanners | O'Brien Arena |
| February 12, 2025 | (1) Lexington Minutemen at (7) Winchester Red & Black | O'Brien Arena |
| February 15, 2025 | (0) Winchester Red & Black at (4) Reading Rockets | Burbank Ice Arena |
| February 19, 2025 | (2) Winchester Red & Black at (2) Milton Wildcats | Ulin Memorial Rink |
| February 25, 2025 | (1) Winchester Red & Black at (0) St. Mary's Lynn Spartans
MIAA D1 Girls State Tournament - Round of 32 |
Connery Memorial Arena |
| February 28, 2025 | (1) Winchester Red & Black at (2) Malden Catholic Lancers
MIAA D1 Girls State Tournament - Round of 16 |
Valley Forum II |
