| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2015 | (1) St. Mary's Lynn Spartans at (0) Winchester Red & Black | O'Brien Arena |
| December 15, 2015 | (1) Stoneham Spartans at (3) Winchester Red & Black | O'Brien Arena |
| December 19, 2015 | (5) Winchester Red & Black at (0) Watertown Raiders | John A. Ryan Arena |
| December 23, 2015 | (3) Winchester Red & Black at (1) Burlington Red Devils | Burlington Ice Palace |
| January 02, 2016 | (0) Winchester Red & Black at (1) Woburn Tanners | O'Brien Arena |
| January 06, 2016 | (2) Winchester Red & Black at (4) Lexington Minutemen | Edge Sports Center |
| January 09, 2016 | (1) Reading Rockets at (2) Winchester Red & Black | O'Brien Arena |
| January 13, 2016 | (2) Belmont/Watertown Marauders at (11) Winchester Red & Black | O'Brien Arena |
| January 16, 2016 | (5) Arlington Spy Ponders at (4) Winchester Red & Black | O'Brien Arena |
| January 20, 2016 | (0) Wakefield Warriors at (8) Winchester Red & Black | O'Brien Arena |
| January 23, 2016 | (0) Wilmington Wildcats at (7) Winchester Red & Black | O'Brien Arena |
| January 27, 2016 | (0) Melrose Red Hawks at (4) Winchester Red & Black | O'Brien Arena |
| January 30, 2016 | (4) Woburn Tanners at (5) Winchester Red & Black | O'Brien Arena |
| February 02, 2016 | (1) Lexington Minutemen at (4) Winchester Red & Black | O'Brien Arena |
| February 06, 2016 | (0) Winchester Red & Black at (4) Reading Rockets | Burbank Ice Arena |
| February 10, 2016 | (10) Winchester Red & Black at (0) Belmont/Watertown Marauders | Skip Viglirolo Rink |
| February 13, 2016 | (3) Winchester Red & Black at (0) Arlington Spy Ponders | Ed Burns Arena |
| February 16, 2016 | (11) Winchester Red & Black at (0) Marblehead Magicians
Newburyport Bank Classic |
O'Brien Arena |
| February 18, 2016 | (2) Masconomet Chieftains at (5) Winchester Red & Black
Newburyport Bank Classic Championship Game |
Graf Rink |
| February 20, 2016 | (0) Tewksbury/Methuen Red Rangers at (1) Winchester Red & Black | O'Brien Arena |
| February 29, 2016 | (0) Canton Bulldogs at (2) Winchester Red & Black | O'Brien Arena |
| March 05, 2016 | (2) Notre Dame Academy (Hingham) Cougars at (1) Winchester Red & Black | O'Brien Arena |
