| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2015 | (4) Winchester Red & Black at (1) Falmouth Clippers | Falmouth Ice Arena |
| December 15, 2015 | (1) Stoneham Spartans at (3) Winchester Red & Black | O'Brien Arena |
| December 19, 2015 | (4) Winchester Red & Black at (2) Watertown/Wayland Raiders | John A. Ryan Arena |
| December 23, 2015 | (3) Winchester Red & Black at (1) Burlington Red Devils | Burlington Ice Palace |
| January 02, 2016 | (5) Winchester Red & Black at (5) Woburn Tanners | O'Brien Arena |
| January 06, 2016 | (5) Winchester Red & Black at (1) Lexington Minutemen | Edge Sports Center |
| January 09, 2016 | (0) Reading Rockets at (2) Winchester Red & Black | O'Brien Arena |
| January 11, 2016 | (1) Winchester Red & Black at (3) BC High Eagles | Clark Athletic Center |
| January 13, 2016 | (1) Belmont Marauders at (5) Winchester Red & Black | O'Brien Arena |
| January 16, 2016 | (2) Arlington Spy Ponders at (4) Winchester Red & Black | O'Brien Arena |
| January 20, 2016 | (0) Wakefield Warriors at (3) Winchester Red & Black | O'Brien Arena |
| January 23, 2016 | (1) Winchester Red & Black at (0) Wilmington Wildcats | Ristuccia Memorial Arena |
| January 27, 2016 | (1) Melrose Red Hawks at (4) Winchester Red & Black | O'Brien Arena |
| January 30, 2016 | (2) Woburn Tanners at (1) Winchester Red & Black | O'Brien Arena |
| February 01, 2016 | (2) Winchester Red & Black at (6) Hingham Harbormen | Pilgrim Arena |
| February 03, 2016 | (0) Lexington Minutemen at (4) Winchester Red & Black | O'Brien Arena |
| February 06, 2016 | (0) Winchester Red & Black at (3) Reading Rockets | Burbank Ice Arena |
| February 10, 2016 | (5) Winchester Red & Black at (2) Belmont Marauders | Skip Viglirolo Rink |
| February 13, 2016 | (1) Winchester Red & Black at (4) Arlington Spy Ponders | Ed Burns Arena |
| February 15, 2016 | (4) Winchester Red & Black at (1) Wellesley Raiders | Babson Skating Center |
| February 24, 2016 | (0) Medford Mustangs at (7) Winchester Red & Black | O'Brien Arena |
| March 02, 2016 | (1) Medford Mustangs at (6) Winchester Red & Black | Arlington Sports Center |
| March 05, 2016 | (3) Arlington Catholic Cougars at (0) Winchester Red & Black | Chelmsford Forum |
