| Date & Time | Game | Venue |
|---|---|---|
| December 13, 2023 | (0) Wilmington Wildcats at (6) Winchester Red & Black | O'Brien Arena |
| December 16, 2023 | (2) Stoneham Spartans at (7) Winchester Red & Black | O'Brien Arena |
| December 20, 2023 | (5) Winchester Red & Black at (1) Melrose Red Hawks | Kasabuski Arena |
| December 23, 2023 | (2) Winchester Red & Black at (3) St. Mary's Lynn Spartans | Connery Memorial Arena |
| December 29, 2023 | (6) Reading Rockets at (1) Winchester Red & Black | O'Brien Arena |
| January 03, 2024 | (1) Winchester Red & Black at (3) Belmont Marauders | John A. Ryan Arena |
| January 06, 2024 | (4) Arlington Spy Ponders at (1) Winchester Red & Black | O'Brien Arena |
| January 10, 2024 | (2) Woburn Tanners at (5) Winchester Red & Black | O'Brien Arena |
| January 13, 2024 | (2) Winchester Red & Black at (4) Hingham Harbormen | Pilgrim Arena |
| January 15, 2024 | (6) Winchester Red & Black at (3) Malden Catholic Lancers | Valley Forum II |
| January 20, 2024 | (2) Winchester Red & Black at (0) Reading Rockets | Burbank Ice Arena |
| January 24, 2024 | (4) Winchester Red & Black at (1) Wakefield Warriors | Stoneham Arena |
| January 26, 2024 | (5) Winchester Red & Black at (3) Watertown/Wayland Raiders | John A. Ryan Arena |
| January 28, 2024 | (0) Winchester Red & Black at (3) Tewksbury Redmen
Ed Burns Coffee Pot |
Ed Burns Arena |
| January 31, 2024 | (1) Winchester Red & Black at (2) Burlington Red Devils | Burlington Ice Palace |
| February 02, 2024 | (0) Belmont Marauders at (2) Winchester Red & Black | O'Brien Arena |
| February 04, 2024 | (5) Winchester Red & Black at (1) Weymouth Wildcats
Ed Burns Coffee Pot |
Rodman Arena |
| February 07, 2024 | (2) Winchester Red & Black at (2) Arlington Spy Ponders | Ed Burns Arena |
| February 10, 2024 | (7) Winchester Red & Black at (4) Woburn Tanners | O'Brien Arena |
| February 11, 2024 | (3) Winchester Red & Black at (1) Canton Bulldogs
Ed Burns Coffee Pot |
Canton Ice House |
| February 15, 2024 | (2) Winchester Red & Black at (4) Pope Francis Cardinals | Olympia Center |
| February 21, 2024 | (0) Winchester Red & Black at (3) Catholic Memorial Knights | Warrior Ice Arena |
| February 28, 2024 | (2) Waltham Hawks at (3) Winchester Red & Black
MIAA D1 BOYS STATE TOURNAMENT - Round 32-OT win |
O'Brien Arena |
| March 02, 2024 | (3) Winchester Red & Black at (2) Arlington Spy Ponders
MIAA D1 BOYS STATE TOURNAMENT - SWEET 16 (2 OT) |
Ed Burns Arena |
| March 06, 2024 | (4) Winchester Red & Black at (1) Catholic Memorial Knights
MIAA D1 Boys State Tournament - Elite 8 |
Loring Arena |
| March 09, 2024 | (3) Winchester Red & Black at (2) Arlington Catholic Cougars
MIAA D1 BOYS STATE TOURNAMENT - Final 4 |
Loring Arena |
| March 17, 2024 | (2) Winchester Red & Black at (3) St. John's Prep Eagles
MIAA D1 BOYS STATE TOURNAMENT - State Championship |
TD Garden |
