| Date & Time | Game | Venue |
|---|---|---|
| Dec. 14, 4:00 PM | (5) Winchester Red & Black at (0) Wilmington Wildcats | Breakaway Ice Center |
| Dec. 18, 6:00 PM | (5) Winchester Red & Black at (2) Stoneham Spartans | Stoneham Arena |
| Dec. 21, 12:00 PM | (1) Melrose Red Hawks at (5) Winchester Red & Black | O'Brien Arena |
| Dec. 23, 5:00 PM | (4) St. Mary's Lynn Spartans at (3) Winchester Red & Black | O'Brien Arena |
| Dec. 28, 6:00 PM | (4) Winchester Red & Black at (2) Reading Rockets | Burbank Ice Arena |
| Dec. 31, 12:30 PM | (0) Malden Catholic Lancers at (3) Winchester Red & Black | O'Brien Arena |
| Jan. 4, 12:00 PM | (4) Belmont Marauders at (1) Winchester Red & Black | O'Brien Arena |
| Jan. 8, 6:00 PM | (2) Winchester Red & Black at (3) Arlington Spy Ponders
Arlington wins in OT |
Ed Burns Arena |
| Jan. 11, 12:00 PM | (1) Winchester Red & Black at (3) Woburn Tanners | O'Brien Arena |
| Jan. 13, 5:00 PM | (5) Hingham Harbormen at (3) Winchester Red & Black | O'Brien Arena |
| Jan. 18, 12:00 PM | (3) Reading Rockets at (0) Winchester Red & Black | O'Brien Arena |
| Jan. 22, 5:00 PM | (1) Wakefield Warriors at (7) Winchester Red & Black | O'Brien Arena |
| Jan. 24, 6:00 PM | (3) Watertown/Wayland Raiders at (6) Winchester Red & Black | O'Brien Arena |
| Jan. 26, 12:00 PM | (3) Winchester Red & Black at (5) Hingham Harbormen
Ed Burns Tournament |
Ed Burns Arena |
| Jan. 29, 7:00 PM | (0) Burlington Red Devils at (2) Winchester Red & Black | O'Brien Arena |
| Jan. 31, 7:50 PM | (1) Winchester Red & Black at (3) Belmont Marauders | John A. Ryan Arena |
| Feb. 2, 3:30 PM | (1) Concord-Carlisle Patriots at (4) Winchester Red & Black
Ed Burns Coffee Pot Tournament - Doherty Consolation |
Chelmsford Forum |
| Feb. 5, 7:00 PM | (6) Arlington Spy Ponders at (1) Winchester Red & Black | O'Brien Arena |
| Feb. 7, 6:00 PM | (2) Woburn Tanners at (2) Winchester Red & Black
Winchester wins in OT |
O'Brien Arena |
| Feb. 12, 7:00 PM | (4) Pope Francis Cardinals at (1) Winchester Red & Black | O'Brien Arena |
| Feb. 17, 3:00 PM | (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 |
| Feb. 19, 5:00 PM | (3) Catholic Memorial Knights at (2) Winchester Red & Black
CM wins in OT |
O'Brien Arena |
| Feb. 25, 7:00 PM | (1) Shrewsbury Colonials at (4) Winchester Red & Black
MIAA D1 BOYS STATE TOURNAMENT - Round 32 |
O'Brien Arena |
| Mar. 2, 6:00 PM | (2) Winchester Red & Black at (1) Belmont Marauders
MIAA D1 Boys State Tournament - Round of 16 - Winchester Win 3OT |
John A. Ryan Arena |
| Mar. 6, 7:20 PM | (4) Saint John's Shrewsbury Pioneers at (3) Winchester Red & Black
MIAA D1 BOYS STATE TOURNAMENT - Round 8 (SJS WINS IN OT) |
Chelmsford Forum |
