| Date & Time | Game | Venue |
|---|---|---|
| December 13, 2025 | (2) Stoneham/Wilmington Spartans at (7) Winchester Red & Black | O'Brien Arena |
| December 17, 2025 | (4) Winchester Red & Black at (0) Melrose Red Hawks | Flynn Memorial Rink |
| December 20, 2025 | (3) Winchester Red & Black at (4) Wakefield Warriors | Stoneham Arena |
| December 27, 2025 | (2) Tewksbury/Methuen Red Rangers at (1) Winchester Red & Black | O'Brien Arena |
| Dec. 29 Postponed | Nantucket Whalers at Winchester Red & Black
Makeup TBD |
O'Brien Arena |
| December 31, 2025 | (1) Winchester Red & Black at (3) Pope Francis Cardinals | Smead Arena at Blunt Park |
| January 03, 2026 | (0) Arlington Spy Ponders at (1) Winchester Red & Black | O'Brien Arena |
| January 07, 2026 | (3) Woburn Tanners at (2) Winchester Red & Black
Woburn wins in OT |
O'Brien Arena |
| January 10, 2026 | (1) Lexington Minutemen at (4) Winchester Red & Black | O'Brien Arena |
| January 14, 2026 | (0) Winchester Red & Black at (4) Reading Rockets | Burbank Ice Arena |
| January 17, 2026 | (3) Winchester Red & Black at (2) Belmont Marauders | Skip Viglirolo Rink |
| January 19, 2026 | (0) Beverly/Danvers/Ipswich Panthers at (3) Winchester Red & Black | O'Brien Arena |
| January 21, 2026 | (2) Winchester Red & Black at (3) Malden Catholic Lancers
Malden Catholic wins in OT |
Valley Forum II |
| January 24, 2026 | (4) Winchester Red & Black at (1) Burlington Red Devils | Burlington Ice Palace |
| January 28, 2026 | (2) Masconomet Chieftains at (4) Winchester Red & Black | O'Brien Arena |
| January 31, 2026 | (3) Winchester Red & Black at (1) Arlington Spy Ponders | Ed Burns Arena |
| February 04, 2026 | (1) Winchester Red & Black at (2) Woburn Tanners | O'Brien Arena |
| February 07, 2026 | (2) Winchester Red & Black at (0) Lexington Minutemen | Hayden Ice Facility |
| February 11, 2026 | (2) Reading Rockets at (1) Winchester Red & Black | O'Brien Arena |
| February 14, 2026 | (1) Belmont Marauders at (3) Winchester Red & Black | O'Brien Arena |
| February 15, 2026 | (0) Nantucket Whalers at (6) Winchester Red & Black | O'Brien Arena |
| February 19, 2026 | (3) Winchester Red & Black at (3) Andover Golden Warriors | Breakaway Ice Center |
| February 25, 2026 | (3) Winchester Red & Black at (2) Natick Red Hawks
MIAA D1 - Girls State Tournament - Round 32 |
Chase Arena |
| February 28, 2026 | (2) Winchester Red & Black at (3) St. Mary's Lynn Spartans
MIAA D1 - Boys State Tournament - Round 16 |
Connery Memorial Arena |
