| Date & Time | Game | Venue |
|---|---|---|
| December 13, 2023 | (3) Pembroke Titans at (0) Winchester Red & Black | O'Brien Arena |
| December 16, 2023 | (1) Stoneham/Wilmington Spartans at (3) Winchester Red & Black | O'Brien Arena |
| December 20, 2023 | (6) Winchester Red & Black at (2) Melrose Red Hawks | Flynn Memorial Rink |
| December 23, 2023 | (2) Winchester Red & Black at (1) Archbishop Williams Bishops | O'Brien Arena |
| January 04, 2024 | (0) Winchester Red & Black at (1) Belmont Marauders | John A. Ryan Arena |
| January 06, 2024 | (1) Arlington Spy Ponders at (5) Winchester Red & Black | O'Brien Arena |
| January 08, 2024 | (8) Hingham Harborwomen at (1) Winchester Red & Black | O'Brien Arena |
| January 10, 2024 | (2) Woburn Tanners at (1) Winchester Red & Black
Woburn wins in OT |
O'Brien Arena |
| January 13, 2024 | (0) Lexington Minutemen at (3) Winchester Red & Black | O'Brien Arena |
| January 15, 2024 | (0) Winchester Red & Black at (4) Malden Catholic Lancers | Valley Forum II |
| January 17, 2024 | (0) Winchester Red & Black at (3) Winthrop Vikings | Larsen Rink |
| January 20, 2024 | (4) Winchester Red & Black at (1) Reading Rockets | Burbank Ice Arena |
| January 24, 2024 | (6) Winchester Red & Black at (1) Wakefield Warriors | Stoneham Arena |
| January 27, 2024 | (3) Winchester Red & Black at (3) Andover Golden Warriors | Breakaway Ice Center |
| January 31, 2024 | (0) Winchester Red & Black at (3) Burlington Red Devils | Burlington Ice Palace |
| February 03, 2024 | (2) Belmont Marauders at (0) Winchester Red & Black | O'Brien Arena |
| February 07, 2024 | (1) Winchester Red & Black at (3) Arlington Spy Ponders | Ed Burns Arena |
| February 10, 2024 | (2) Winchester Red & Black at (2) Woburn Tanners | O'Brien Arena |
| February 14, 2024 | (1) Winchester Red & Black at (0) Lexington Minutemen | Hayden Ice Facility |
| February 17, 2024 | (2) Reading Rockets at (3) Winchester Red & Black | O'Brien Arena |
| February 28, 2024 | (0) Winchester Red & Black at (1) Peabody/Lynnfield/North Reading Tanners
MIAA D1 Girls State Tournament - First Round |
McVann-O'Keefe Skating Rink |
