| Date & Time | Game | Venue |
|---|---|---|
| Dec. 13, 12:00 PM | (2) Stoneham/Wilmington Spartans at (7) Winchester Red & Black | O'Brien Arena |
| Dec. 17, 6:00 PM | (4) Winchester Red & Black at (0) Melrose Red Hawks | Flynn Memorial Rink |
| Dec. 20, 6:00 PM | (3) Winchester Red & Black at (4) Wakefield Warriors | Stoneham Arena |
| Dec. 27, 12:00 PM | (2) Tewksbury/Methuen Red Rangers at (1) Winchester Red & Black | O'Brien Arena |
| Dec. 29 Postponed | Nantucket Whalers at Winchester Red & Black
Makeup TBD |
O'Brien Arena |
| Dec. 31, 12:30 PM | (1) Winchester Red & Black at (3) Pope Francis Cardinals | Smead Arena at Blunt Park |
| Jan. 3, 12:00 PM | (0) Arlington Spy Ponders at (1) Winchester Red & Black | O'Brien Arena |
| Jan. 7, 5:00 PM | (3) Woburn Tanners at (2) Winchester Red & Black
Woburn wins in OT |
O'Brien Arena |
| Jan. 10, 12:00 PM | (1) Lexington Minutemen at (4) Winchester Red & Black | O'Brien Arena |
| Jan. 14, 6:00 PM | (0) Winchester Red & Black at (4) Reading Rockets | Burbank Ice Arena |
| Jan. 17, 1:00 PM | (3) Winchester Red & Black at (2) Belmont Marauders | Skip Viglirolo Rink |
| Jan. 19, 10:00 AM | (0) Beverly/Danvers/Ipswich Panthers at (3) Winchester Red & Black | O'Brien Arena |
| Jan. 21, 5:00 PM | (2) Winchester Red & Black at (3) Malden Catholic Lancers
Malden Catholic wins in OT |
Valley Forum II |
| Jan. 24, 2:15 PM | (4) Winchester Red & Black at (1) Burlington Red Devils | Burlington Ice Palace |
| Jan. 28, 7:00 PM | (2) Masconomet Chieftains at (4) Winchester Red & Black | O'Brien Arena |
| Jan. 31, 2:25 PM | (3) Winchester Red & Black at (1) Arlington Spy Ponders | Ed Burns Arena |
| Feb. 4, 5:00 PM | (1) Winchester Red & Black at (2) Woburn Tanners | O'Brien Arena |
| Feb. 7, 7:15 PM | (2) Winchester Red & Black at (0) Lexington Minutemen | Hayden Ice Facility |
| Feb. 11, 7:00 PM | (2) Reading Rockets at (1) Winchester Red & Black | O'Brien Arena |
| Feb. 14, 2:00 PM | (1) Belmont Marauders at (3) Winchester Red & Black | O'Brien Arena |
| Feb. 15, 12:00 PM | (0) Nantucket Whalers at (6) Winchester Red & Black | O'Brien Arena |
| Feb. 19, 2:50 PM | (3) Winchester Red & Black at (3) Andover Golden Warriors | Breakaway Ice Center |
| Feb. 25, 7:40 PM | (3) Winchester Red & Black at (2) Natick Red Hawks
MIAA D1 - Girls State Tournament - Round 32 |
Chase Arena |
| Feb. 28, 2:00 PM | (2) Winchester Red & Black at (3) St. Mary's Lynn Spartans
MIAA D1 - Boys State Tournament - Round 16 |
Connery Memorial Arena |