| Date & Time | Game | Venue |
|---|---|---|
| December 08, 2018 | (1) Winchester Red & Black at (0) Milton Wildcats | Ulin Memorial Rink |
| December 11, 2018 | (4) Wakefield Warriors at (4) Winchester Red & Black | O'Brien Arena |
| December 15, 2018 | (6) Winchester Red & Black at (3) Watertown Raiders | John A. Ryan Arena |
| December 18, 2018 | (1) Burlington Red Devils at (6) Winchester Red & Black | O'Brien Arena |
| December 22, 2018 | (1) Lexington Minutemen at (1) Winchester Red & Black | O'Brien Arena |
| December 29, 2018 | (3) Notre Dame Academy (Hingham) Cougars at (1) Winchester Red & Black | O'Brien Arena |
| January 05, 2019 | (2) Winchester Red & Black at (2) Reading Rockets | Burbank Ice Arena |
| January 09, 2019 | (0) Belmont/Watertown Marauders at (6) Winchester Red & Black | O'Brien Arena |
| January 12, 2019 | (4) Arlington Spy Ponders at (4) Winchester Red & Black | O'Brien Arena |
| January 16, 2019 | (0) Woburn Tanners at (2) Winchester Red & Black | O'Brien Arena |
| January 19, 2019 | (2) Winchester Red & Black at (0) Wilmington Wildcats | Ristuccia Memorial Arena |
| January 21, 2019 | (10) Winchester Red & Black at (5) Quincy/North Quincy Red Raiders | Quincy Youth Arena |
| January 26, 2019 | (3) Stoneham Spartans at (1) Winchester Red & Black | O'Brien Arena |
| January 30, 2019 | (2) Winchester Red & Black at (2) Melrose Red Hawks | Flynn Memorial Rink |
| February 02, 2019 | (1) Winchester Red & Black at (3) Lexington Minutemen | Edge Sports Center |
| February 06, 2019 | (3) Reading Rockets at (3) Winchester Red & Black | O'Brien Arena |
| February 09, 2019 | (0) Winchester Red & Black at (3) Belmont/Watertown Marauders | O'Brien Arena |
| February 13, 2019 | (0) Winchester Red & Black at (2) Arlington Spy Ponders | Ed Burns Arena |
| February 16, 2019 | (1) Winchester Red & Black at (3) Woburn Tanners | O'Brien Arena |
| February 18, 2019 | (2) Milton Wildcats at (3) Winchester Red & Black | O'Brien Arena |
| February 20, 2019 | (2) Winchester Red & Black at (2) Winthrop Vikings | Larsen Rink |
| February 27, 2019 | (1) Archbishop Williams Bishops at (4) Winchester Red & Black | O'Brien Arena |
| March 03, 2019 | (1) Winchester Red & Black at (2) Walpole Timberwolves
Overtime |
Canton Ice House |
