| Date & Time | Game | Venue |
|---|---|---|
| Dec. 13, 2:00 PM | (2) Stoneham Spartans at (3) Winchester Red & Black
Winchester Win in OT |
O'Brien Arena |
| Dec. 17, 7:40 PM | (2) Winchester Red & Black at (0) Melrose Red Hawks | Kasabuski Arena |
| Dec. 20, 4:00 PM | (3) Winchester Red & Black at (2) Wakefield Warriors
Winchester wins in OT |
Stoneham Arena |
| Dec. 23, 5:00 PM | (2) Xaverian Hawks at (1) Winchester Red & Black | O'Brien Arena |
| Jan. 3, 2:00 PM | (1) Arlington Spy Ponders at (2) Winchester Red & Black | O'Brien Arena |
| Jan. 7, 7:00 PM | (2) Woburn Tanners at (1) Winchester Red & Black | O'Brien Arena |
| Jan. 10, 6:00 PM | (1) Winchester Red & Black at (7) Hingham Harbormen | Pilgrim Arena |
| Jan. 14, 7:45 PM | (1) Winchester Red & Black at (2) Reading Rockets | Burbank Ice Arena |
| Jan. 17, 3:00 PM | (3) Winchester Red & Black at (1) Belmont Marauders | Skip Viglirolo Rink |
| Jan. 21, 4:00 PM | (3) Winchester Red & Black at (2) Watertown/Wayland Raiders | John A. Ryan Arena |
| Jan. 24, 4:15 PM | (1) Winchester Red & Black at (4) Burlington Red Devils | Burlington Ice Palace |
| Jan. 25, 11:00 AM | (0) Franklin Panthers at (6) Winchester Red & Black
Ed Burns Tournament |
Canton Ice House |
| Jan. 28, 5:00 PM | (0) Wilmington Wildcats at (9) Winchester Red & Black | O'Brien Arena |
| Jan. 31, 12:40 PM | (1) Winchester Red & Black at (5) Arlington Spy Ponders | Ed Burns Arena |
| Feb. 1, 2:20 PM | (0) Walpole Timberwolves at (2) Winchester Red & Black
Ed Burns Tournament |
Cadillac Ice Arena |
| Feb. 4, 7:00 PM | Winchester Red & Black at Woburn Tanners | O'Brien Arena |
| Feb. 7, 4:00 PM | Winchester Red & Black at St. Mary's Lynn Spartans | Connery Memorial Arena |
| Feb. 8, 12:00 PM | Winchester Red & Black at TBD
Ed Burns Tournament |
Ed Burns Arena |
| Feb. 11, 5:00 PM | Reading Rockets at Winchester Red & Black | O'Brien Arena |
| Feb. 14, 12:00 PM | Belmont Marauders at Winchester Red & Black | O'Brien Arena |
| Feb. 16, 5:00 PM | Winchester Red & Black at Malden Catholic Lancers | Valley Forum II |
| Feb. 18, 7:00 PM | Winchester Red & Black at Catholic Memorial Knights | Warrior Ice Arena |
