| 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 | Lexington Minutemen at Winchester Red & Black | O'Brien Arena |
| Jan. 14, 6:00 PM | Winchester Red & Black at Reading Rockets | Burbank Ice Arena |
| Jan. 17, 1:00 PM | Winchester Red & Black at Belmont Marauders | Skip Viglirolo Rink |
| Jan. 19, 10:00 AM | Beverly/Danvers/Ipswich Panthers at Winchester Red & Black | O'Brien Arena |
| Jan. 21, 5:00 PM | Winchester Red & Black at Malden Catholic Lancers | Valley Forum II |
| Jan. 24, 2:15 PM | Winchester Red & Black at Burlington Red Devils | Burlington Ice Palace |
| Jan. 28, 7:00 PM | Masconomet Chieftains at Winchester Red & Black | O'Brien Arena |
| Jan. 31, 2:25 PM | Winchester Red & Black at Arlington Spy Ponders | Ed Burns Arena |
| Feb. 4, 5:00 PM | Winchester Red & Black at Woburn Tanners | O'Brien Arena |
| Feb. 7, 7:15 PM | Winchester Red & Black at Lexington Minutemen | Hayden Ice Facility |
| Feb. 11, 7:00 PM | Reading Rockets at Winchester Red & Black | O'Brien Arena |
| Feb. 14, 2:00 PM | Belmont Marauders at Winchester Red & Black | O'Brien Arena |
| Feb. 19, 2:50 PM | Winchester Red & Black at Andover Golden Warriors | Breakaway Ice Center |
