| Date & Time | Game | Venue |
|---|---|---|
| December 11, 2022 | (8) Winchester Red & Black at (0) Old Rochester Bulldogs | Falmouth Ice Arena |
| December 14, 2022 | (4) Burlington Red Devils at (1) Winchester Red & Black | O'Brien Arena |
| December 21, 2022 | (5) Winchester Red & Black at (0) Stoneham/Wilmington Spartans | Stoneham Arena |
| January 04, 2023 | (1) Reading Rockets at (0) Winchester Red & Black | O'Brien Arena |
| January 09, 2023 | (2) Winchester Red & Black at (3) Hingham Harborwomen | Pilgrim Arena |
| January 11, 2023 | (3) Winchester Red & Black at (1) Arlington Spy Ponders | Ed Burns Arena |
| January 14, 2023 | (6) Winchester Red & Black at (0) Woburn Tanners | O'Brien Arena |
| January 16, 2023 | (1) Malden Catholic Lancers at (2) Winchester Red & Black | O'Brien Arena |
| January 21, 2023 | (6) Winchester Red & Black at (0) Lexington Minutemen | Hayden Ice Facility |
| January 24, 2023 | (2) Melrose Red Hawks at (8) Winchester Red & Black | O'Brien Arena |
| January 28, 2023 | (1) Wakefield Warriors at (6) Winchester Red & Black | O'Brien Arena |
| January 30, 2023 | (0) Lincoln-Sudbury Warriors at (4) Winchester Red & Black | Hobomock Arena |
| February 01, 2023 | (0) Belmont/Watertown Marauders at (2) Winchester Red & Black | O'Brien Arena |
| February 04, 2023 | (0) Winchester Red & Black at (1) Reading Rockets | Burbank Ice Arena |
| February 08, 2023 | (2) Winchester Red & Black at (2) Belmont/Watertown Marauders | Skip Viglirolo Rink |
| February 11, 2023 | (1) Arlington Spy Ponders at (5) Winchester Red & Black | O'Brien Arena |
| February 15, 2023 | (2) Woburn Tanners at (4) Winchester Red & Black | O'Brien Arena |
| February 18, 2023 | (2) Lexington Minutemen at (6) Winchester Red & Black | O'Brien Arena |
| February 21, 2023 | (5) Duxbury Dragons at (1) Winchester Red & Black
Hingham Showcase |
Pilgrim Arena |
| February 23, 2023 | (2) Archbishop Williams Bishops at (0) Winchester Red & Black
Hingham Showcase |
Pilgrim Arena |
| March 01, 2023 | (1) Waltham Hawks at (2) Winchester Red & Black
MIAA D2 Girls State Tournament - First Round |
O'Brien Arena |
| March 04, 2023 | (1) Winchester Red & Black at (2) Burlington Red Devils
MIAA D2 Girls State Tournament |
O'Brien Arena |
