| Date & Time | Game | Venue |
|---|---|---|
| Dec. 13, 7:00 PM | (0) Wilmington Wildcats at (6) Winchester Red & Black | O'Brien Arena |
| Dec. 16, 2:00 PM | (2) Stoneham Spartans at (7) Winchester Red & Black | O'Brien Arena |
| Dec. 20, 7:45 PM | (5) Winchester Red & Black at (1) Melrose Red Hawks | Kasabuski Arena |
| Dec. 23, 4:00 PM | (2) Winchester Red & Black at (3) St. Mary's Lynn Spartans | Connery Memorial Arena |
| Dec. 29, 5:00 PM | (6) Reading Rockets at (1) Winchester Red & Black | O'Brien Arena |
| Jan. 3, 6:00 PM | (1) Winchester Red & Black at (3) Belmont Marauders | John A. Ryan Arena |
| Jan. 6, 2:00 PM | (4) Arlington Spy Ponders at (1) Winchester Red & Black | O'Brien Arena |
| Jan. 10, 7:00 PM | (2) Woburn Tanners at (5) Winchester Red & Black | O'Brien Arena |
| Jan. 13, 4:00 PM | (2) Winchester Red & Black at (4) Hingham Harbormen | Pilgrim Arena |
| Jan. 15, 2:40 PM | (6) Winchester Red & Black at (3) Malden Catholic Lancers | Valley Forum II |
| Jan. 20, 6:00 PM | (2) Winchester Red & Black at (0) Reading Rockets | Burbank Ice Arena |
| Jan. 24, 6:00 PM | (4) Winchester Red & Black at (1) Wakefield Warriors | Stoneham Arena |
| Jan. 26, 7:50 PM | (5) Winchester Red & Black at (3) Watertown/Wayland Raiders | John A. Ryan Arena |
| Jan. 28, 6:00 PM | (0) Winchester Red & Black at (3) Tewksbury Redmen
Ed Burns Coffee Pot |
Ed Burns Arena |
| Jan. 31, 5:00 PM | (1) Winchester Red & Black at (2) Burlington Red Devils | Burlington Ice Palace |
| Feb. 2, 6:10 PM | (0) Belmont Marauders at (2) Winchester Red & Black | O'Brien Arena |
| Feb. 4, 2:00 PM | (5) Winchester Red & Black at (1) Weymouth Wildcats
Ed Burns Coffee Pot |
Rodman Arena |
| Feb. 7, 6:00 PM | (2) Winchester Red & Black at (2) Arlington Spy Ponders | Ed Burns Arena |
| Feb. 10, 12:00 PM | (7) Winchester Red & Black at (4) Woburn Tanners | O'Brien Arena |
| Feb. 11, 2:20 PM | (3) Winchester Red & Black at (1) Canton Bulldogs
Ed Burns Coffee Pot |
Canton Ice House |
| Feb. 15, 6:40 PM | (2) Winchester Red & Black at (4) Pope Francis Cardinals | Olympia Center |
| Feb. 21, 7:00 PM | (0) Winchester Red & Black at (3) Catholic Memorial Knights | Warrior Ice Arena |
| Feb. 28, 5:00 PM | (2) Waltham Hawks at (3) Winchester Red & Black
MIAA D1 BOYS STATE TOURNAMENT - Round 32-OT win |
O'Brien Arena |
| Mar. 2, 1:00 PM | (3) Winchester Red & Black at (2) Arlington Spy Ponders
MIAA D1 BOYS STATE TOURNAMENT - SWEET 16 (2 OT) |
Ed Burns Arena |
| Mar. 6, 5:00 PM | (4) Winchester Red & Black at (1) Catholic Memorial Knights
MIAA D1 Boys State Tournament - Elite 8 |
Loring Arena |
| Mar. 9, 7:30 PM | (3) Winchester Red & Black at (2) Arlington Catholic Cougars
MIAA D1 BOYS STATE TOURNAMENT - Final 4 |
Loring Arena |
| Mar. 17, 5:30 PM | (2) Winchester Red & Black at (3) St. John's Prep Eagles
MIAA D1 BOYS STATE TOURNAMENT - State Championship |
TD Garden |
