| Date & Time | Game | Venue |
|---|---|---|
| December 11, 2018 | (1) Wakefield Warriors at (4) Winchester Red & Black | O'Brien Arena |
| December 15, 2018 | (1) Winchester Red & Black at (3) St. Mary's Lynn Spartans | Connery Memorial Arena |
| December 18, 2018 | (3) Burlington Red Devils at (4) Winchester Red & Black | O'Brien Arena |
| December 22, 2018 | (0) Lexington Minutemen at (7) Winchester Red & Black | O'Brien Arena |
| December 27, 2018 | (2) Needham Rockets at (5) Winchester Red & Black | O'Brien Arena |
| December 29, 2018 | (3) Winchester Red & Black at (1) Lincoln-Sudbury Warriors | New England Sports Center |
| January 05, 2019 | (4) Winchester Red & Black at (0) Reading Rockets | Burbank Ice Arena |
| January 09, 2019 | (3) Winchester Red & Black at (1) Belmont Marauders | Skip Viglirolo Rink |
| January 12, 2019 | (6) Arlington Spy Ponders at (1) Winchester Red & Black | O'Brien Arena |
| January 16, 2019 | (3) Woburn Tanners at (5) Winchester Red & Black | O'Brien Arena |
| January 19, 2019 | (4) Winchester Red & Black at (0) Wilmington Wildcats | Ristuccia Memorial Arena |
| January 21, 2019 | (1) Malden Catholic Lancers at (7) Winchester Red & Black | O'Brien Arena |
| January 26, 2019 | (4) Stoneham Spartans at (1) Winchester Red & Black | O'Brien Arena |
| January 30, 2019 | (0) Winchester Red & Black at (4) Melrose Red Hawks | Kasabuski Arena |
| February 02, 2019 | (5) Winchester Red & Black at (1) Lexington Minutemen | Hayden Ice Facility |
| February 06, 2019 | (0) Reading Rockets at (1) Winchester Red & Black | O'Brien Arena |
| February 09, 2019 | (3) Belmont Marauders at (0) Winchester Red & Black | O'Brien Arena |
| February 13, 2019 | (2) Winchester Red & Black at (3) Arlington Spy Ponders | Ed Burns Arena |
| February 16, 2019 | (7) Winchester Red & Black at (3) Woburn Tanners | O'Brien Arena |
| February 19, 2019 | (3) Winchester Red & Black at (1) Newburyport Clippers
Newbuyport Bank Classic |
Graf Rink |
| February 22, 2019 | (2) Andover Golden Warriors at (0) Winchester Red & Black
Newburyport Bank Classic Championship Game |
Graf Rink |
| March 03, 2019 | (2) Bishop Fenwick Crusaders at (3) Winchester Red & Black | Stoneham Arena |
| March 07, 2019 | (4) Winchester Red & Black at (2) Billerica Indians | Tsongas Center |
| March 11, 2019 | (4) Winchester Red & Black at (1) St. John's Prep Eagles | Tsongas Center |
| March 17, 2019 | (3) Duxbury Dragons at (1) Winchester Red & Black | TD Garden |
