| Date & Time | Game | Venue |
|---|---|---|
| Dec. 16, 5:00 PM | (1) Longmeadow Lancers at (2) Winchester Red & Black | O'Brien Arena |
| Dec. 18, 8:00 PM | (7) Winchester Red & Black at (1) Stoneham/Wilmington Spartans | Stoneham Arena |
| Dec. 21, 2:00 PM | (3) Melrose Red Hawks at (2) Winchester Red & Black | O'Brien Arena |
| Dec. 28, 4:00 PM | (3) Andover Golden Warriors at (3) Winchester Red & Black | O'Brien Arena |
| Dec. 30, 6:00 PM | (3) Winchester Red & Black at (4) Tewksbury/Methuen Red Rangers | Methuen High School Rink |
| Jan. 4, 2:00 PM | (0) Belmont/Watertown Marauders at (0) Winchester Red & Black | O'Brien Arena |
| Jan. 8, 8:00 PM | (2) Winchester Red & Black at (1) Arlington Spy Ponders | Ed Burns Arena |
| Jan. 11, 2:00 PM | (0) Winchester Red & Black at (1) Woburn Tanners | O'Brien Arena |
| Jan. 15, 7:15 PM | (4) Winchester Red & Black at (0) Lexington Minutemen | Hayden Ice Facility |
| Jan. 18, 2:00 PM | (3) Reading Rockets at (2) Winchester Red & Black | O'Brien Arena |
| Jan. 20, 2:00 PM | (1) Winchester Red & Black at (3) St. Mary's Lynn Spartans | Connery Memorial Arena |
| Jan. 22, 7:00 PM | (1) Wakefield Warriors at (5) Winchester Red & Black | O'Brien Arena |
| Jan. 25, 12:00 PM | (3) Winthrop Vikings at (2) Winchester Red & Black
Winthrop wins in OT |
O'Brien Arena |
| Jan. 29, 5:00 PM | (1) Burlington Red Devils at (3) Winchester Red & Black | O'Brien Arena |
| Feb. 1, 6:10 PM | (2) Winchester Red & Black at (3) Belmont/Watertown Marauders | John A. Ryan Arena |
| Feb. 5, 5:00 PM | (4) Arlington Spy Ponders at (0) Winchester Red & Black | O'Brien Arena |
| Feb. 8, 12:00 PM | (1) Winchester Red & Black at (2) Woburn Tanners | O'Brien Arena |
| Feb. 12, 5:00 PM | (1) Lexington Minutemen at (7) Winchester Red & Black | O'Brien Arena |
| Feb. 15, 6:00 PM | (0) Winchester Red & Black at (4) Reading Rockets | Burbank Ice Arena |
| Feb. 19, 7:00 PM | (2) Winchester Red & Black at (2) Milton Wildcats | Ulin Memorial Rink |
| Feb. 25, 7:00 PM | (1) Winchester Red & Black at (0) St. Mary's Lynn Spartans
MIAA D1 Girls State Tournament - Round of 32 |
Connery Memorial Arena |
| Feb. 28, 7:30 PM | (1) Winchester Red & Black at (2) Malden Catholic Lancers
MIAA D1 Girls State Tournament - Round of 16 |
Valley Forum II |
