| Date & Time | Game | Venue |
|---|---|---|
| December 10, 2016 | (1) Winchester Red & Black at (2) Lincoln-Sudbury Warriors | New England Sports Center |
| December 14, 2016 | (3) Winchester Red & Black at (0) Stoneham Spartans | Stoneham Arena |
| December 17, 2016 | (5) Winchester Red & Black at (4) Medford Mustangs | LoConte Rink |
| December 21, 2016 | (3) Burlington Red Devils at (1) Winchester Red & Black | O'Brien Arena |
| December 28, 2016 | (8) Hingham Harbormen at (0) Winchester Red & Black | O'Brien Arena |
| December 31, 2016 | (2) Winchester Red & Black at (5) St. Mary's Lynn Spartans | Connery Memorial Arena |
| January 04, 2017 | (2) Woburn Tanners at (4) Winchester Red & Black | O'Brien Arena |
| January 11, 2017 | (1) Winchester Red & Black at (4) Reading Rockets | Burbank Ice Arena |
| January 14, 2017 | (1) Winchester Red & Black at (4) Belmont Marauders | Skip Viglirolo Rink |
| January 16, 2017 | (7) BC High Eagles at (0) Winchester Red & Black | O'Brien Arena |
| January 21, 2017 | (1) Winchester Red & Black at (4) Arlington Spy Ponders | Ed Burns Arena |
| January 24, 2017 | (6) Winchester Red & Black at (4) Wakefield Warriors | Ristuccia Memorial Arena |
| January 28, 2017 | (1) Wilmington Wildcats at (3) Winchester Red & Black | O'Brien Arena |
| February 01, 2017 | (2) Winchester Red & Black at (1) Melrose Red Hawks | Kasabuski Arena |
| February 04, 2017 | (5) Winchester Red & Black at (3) Woburn Tanners | O'Brien Arena |
| February 08, 2017 | (4) Winchester Red & Black at (3) Lexington Minutemen | Hayden Ice Facility |
| February 11, 2017 | (2) Reading Rockets at (3) Winchester Red & Black | O'Brien Arena |
| February 15, 2017 | (2) Belmont Marauders at (3) Winchester Red & Black | O'Brien Arena |
| February 18, 2017 | (8) Arlington Spy Ponders at (0) Winchester Red & Black | O'Brien Arena |
| February 20, 2017 | (1) Lexington Minutemen at (5) Winchester Red & Black | O'Brien Arena |
| February 22, 2017 | (5) Bishop Feehan Shamrocks at (1) Winchester Red & Black | O'Brien Arena |
| March 01, 2017 | (4) Winchester Red & Black at (3) Medford Mustangs | Stoneham Arena |
| March 04, 2017 | (1) Winchester Red & Black at (4) Andover Golden Warriors | Chelmsford Forum |
