| Date & Time | Game | Venue |
|---|---|---|
| December 04, 2022 | (2) Winchester Red & Black at (0) Westford Academy Ghosts
Garrett Reagan Summit Game |
New England Sports Center |
| December 14, 2022 | (1) Burlington Red Devils at (2) Winchester Red & Black | O'Brien Arena |
| Dec. 17 Postponed | Wilmington Wildcats at Winchester Red & Black | O'Brien Arena |
| December 19, 2022 | (2) Winchester Red & Black at (7) BC High Eagles | Ed Barry Rink UMass Boston |
| December 21, 2022 | (1) Winchester Red & Black at (1) Stoneham Spartans | Stoneham Arena |
| December 31, 2022 | (0) Wilmington Wildcats at (6) Winchester Red & Black | O'Brien Arena |
| January 04, 2023 | (7) Reading Rockets at (3) Winchester Red & Black | O'Brien Arena |
| January 07, 2023 | (5) Belmont Marauders at (1) Winchester Red & Black | O'Brien Arena |
| January 11, 2023 | (1) Winchester Red & Black at (2) Arlington Spy Ponders
OT |
Ed Burns Arena |
| January 14, 2023 | (5) Woburn Tanners at (3) Winchester Red & Black | O'Brien Arena |
| January 18, 2023 | (2) Winchester Red & Black at (0) St. Mary's Lynn Spartans | O'Brien Arena |
| January 21, 2023 | (3) Hingham Harbormen at (1) Winchester Red & Black | O'Brien Arena |
| January 24, 2023 | (2) Melrose Red Hawks at (5) Winchester Red & Black | O'Brien Arena |
| January 27, 2023 | (1) Wakefield Warriors at (1) Winchester Red & Black | O'Brien Arena |
| January 29, 2023 | (3) Winchester Red & Black at (2) Walpole Timberwolves
Ed Burns Invitational |
Chase Arena |
| February 01, 2023 | (3) Watertown/Wayland Raiders at (0) Winchester Red & Black | O'Brien Arena |
| February 03, 2023 | (0) Winchester Red & Black at (1) Reading Rockets | Burbank Ice Arena |
| February 05, 2023 | (0) Natick Red Hawks at (3) Winchester Red & Black
Ed Burns Tournament |
Canton Ice House |
| February 08, 2023 | (4) Winchester Red & Black at (3) Belmont Marauders | Skip Viglirolo Rink |
| February 10, 2023 | (3) Arlington Spy Ponders at (6) Winchester Red & Black | O'Brien Arena |
| February 12, 2023 | (1) Winchester Red & Black at (6) Tewksbury Redmen
Ed Burns Tournament - Brinn Division Final |
John A. Ryan Arena |
| February 15, 2023 | (4) Woburn Tanners at (4) Winchester Red & Black | O'Brien Arena |
| February 18, 2023 | (0) Winchester Red & Black at (3) Tewksbury Redmen | Breakaway Ice Center |
| February 22, 2023 | (5) Catholic Memorial Knights at (1) Winchester Red & Black | O'Brien Arena |
| March 02, 2023 | (3) Winchester Red & Black at (5) Saint John's Shrewsbury Pioneers
MIAA D1 Boys State Tournament - Round of 32 |
New England Sports Center |
