| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2016 | (5) Winchester Red & Black at (1) Stoneham Spartans | Stoneham Arena |
| December 17, 2016 | (0) Watertown Raiders at (4) Winchester Red & Black | O'Brien Arena |
| December 21, 2016 | (3) Burlington Red Devils at (6) Winchester Red & Black | O'Brien Arena |
| January 02, 2017 | (1) Medford/Malden Mustangs at (5) Winchester Red & Black | O'Brien Arena |
| January 04, 2017 | (2) Woburn Tanners at (2) Winchester Red & Black | O'Brien Arena |
| January 11, 2017 | (3) Winchester Red & Black at (4) Reading Rockets | Burbank Ice Arena |
| January 14, 2017 | (2) Belmont/Watertown Marauders at (1) Winchester Red & Black | O'Brien Arena |
| January 16, 2017 | (4) Winchester Red & Black at (4) Lexington Minutemen | Edge Sports Center |
| January 21, 2017 | (0) Winchester Red & Black at (0) Arlington Spy Ponders | Ed Burns Arena |
| January 23, 2017 | (1) Winchester Red & Black at (1) Tewksbury/Methuen Red Rangers | Methuen High School Rink |
| January 24, 2017 | (6) Winchester Red & Black at (1) Wakefield Warriors | Stoneham Arena |
| January 28, 2017 | (5) Winchester Red & Black at (1) Wilmington Wildcats | Ristuccia Memorial Arena |
| February 01, 2017 | (4) Winchester Red & Black at (0) Melrose Red Hawks | Kasabuski Arena |
| February 04, 2017 | (2) Winchester Red & Black at (3) Woburn Tanners | O'Brien Arena |
| February 11, 2017 | (6) Reading Rockets at (7) Winchester Red & Black | O'Brien Arena |
| February 15, 2017 | (4) Winchester Red & Black at (1) Belmont/Watertown Marauders | Skip Viglirolo Rink |
| February 18, 2017 | (2) Arlington Spy Ponders at (0) Winchester Red & Black | O'Brien Arena |
| February 20, 2017 | (2) Lexington Minutemen at (3) Winchester Red & Black | O'Brien Arena |
| February 21, 2017 | (9) Winchester Red & Black at (0) Marblehead Magicians
Newbury Bank Classic |
Graf Rink |
| February 23, 2017 | (4) Winchester Red & Black at (1) Masconomet Chieftains
Newburyport Bank Classic Championship Game |
Graf Rink |
| February 27, 2017 | (0) Dennis-Yarmouth Dolphins at (4) Winchester Red & Black
Div. 2 Preliminary Round |
O'Brien Arena |
| March 05, 2017 | (2) Winchester Red & Black at (0) Whitman-Hanson/Silver Lake Panthers | The Bog |
| March 11, 2017 | (2) Winchester Red & Black at (3) Canton Bulldogs
Div. 2 Quarterfinals |
Gallo Arena |
