| Date & Time | Game | Venue |
|---|---|---|
| December 16, 2017 | (7) Winchester Red & Black at (0) Wakefield Warriors | Burbank Ice Arena |
| December 19, 2017 | (2) Watertown Raiders at (4) Winchester Red & Black | O'Brien Arena |
| December 23, 2017 | (6) Winchester Red & Black at (3) Burlington Red Devils | Burlington Ice Palace |
| January 03, 2018 | (4) Winchester Red & Black at (1) Lexington Minutemen | Edge Sports Center |
| January 06, 2018 | (1) Reading Rockets at (3) Winchester Red & Black | O'Brien Arena |
| January 10, 2018 | (5) Winchester Red & Black at (3) Belmont Marauders | Skip Viglirolo Rink |
| January 13, 2018 | (1) Winchester Red & Black at (3) Arlington Spy Ponders | Ed Burns Arena |
| January 18, 2018 | (2) Winchester Red & Black at (4) Notre Dame Academy (Hingham) Cougars | Rockland Arena |
| January 20, 2018 | (0) Winchester Red & Black at (3) Woburn Tanners | O'Brien Arena |
| January 23, 2018 | (0) Wilmington Wildcats at (4) Winchester Red & Black | O'Brien Arena |
| January 27, 2018 | (1) Winchester Red & Black at (1) Stoneham Spartans | Stoneham Arena |
| January 29, 2018 | (6) Tewksbury/Methuen Red Rangers at (2) Winchester Red & Black | O'Brien Arena |
| January 30, 2018 | (3) Melrose Red Hawks at (2) Winchester Red & Black | O'Brien Arena |
| February 03, 2018 | (1) Lexington Minutemen at (4) Winchester Red & Black | O'Brien Arena |
| February 08, 2018 | (3) Winchester Red & Black at (3) Reading Rockets
rescheduled from February 7th |
Burbank Ice Arena |
| February 10, 2018 | (5) Belmont Marauders at (1) Winchester Red & Black | O'Brien Arena |
| February 14, 2018 | (1) Arlington Spy Ponders at (1) Winchester Red & Black | O'Brien Arena |
| February 17, 2018 | (3) Woburn Tanners at (1) Winchester Red & Black | O'Brien Arena |
| February 20, 2018 | (0) St. Peter Marian Guardians at (6) Winchester Red & Black | Graf Rink |
| February 22, 2018 | (4) Masconomet Chieftains at (2) Winchester Red & Black
NEWBURYPORT BANK CLASSIC - WINCHESTER-ST PETER MARIAN / TEWSKBURY METHUEN / MASCONOMET |
Graf Rink |
| February 26, 2018 | (0) Wakefield Warriors at (2) Winchester Red & Black | O'Brien Arena |
| March 03, 2018 | (2) Winchester Red & Black at (3) Wellesley / Lincoln Sudbury Raiders | Babson Skating Center |
