| Date & Time | Game | Venue |
|---|---|---|
| December 13, 2019 | (0) Winchester Red & Black at (3) Notre Dame Academy (Hingham) Cougars | Rockland Arena |
| December 14, 2019 | (5) Winchester Red & Black at (1) Watertown Raiders | John A. Ryan Arena |
| December 18, 2019 | (2) Burlington Red Devils at (7) Winchester Red & Black | O'Brien Arena |
| December 21, 2019 | (2) Winchester Red & Black at (1) Wilmington Wildcats | Ristuccia Memorial Arena |
| December 23, 2019 | (7) Barrington High School at (4) Winchester Red & Black | O'Brien Arena |
| December 30, 2019 | (3) Austin Prep Cougars at (0) Winchester Red & Black | Essex Sports Center |
| December 31, 2019 | (0) Winchester Red & Black at (1) Lexington Minutemen | Hayden Ice Facility |
| January 04, 2020 | (1) Reading Rockets at (0) Winchester Red & Black | O'Brien Arena |
| January 08, 2020 | (3) Winchester Red & Black at (3) Belmont Marauders | Skip Viglirolo Rink |
| January 14, 2020 | (1) Winchester Red & Black at (4) Woburn Tanners | O'Brien Arena |
| January 18, 2020 | (5) Winchester Red & Black at (0) Stoneham Spartans | Stoneham Arena |
| January 22, 2020 | (1) Winchester Red & Black at (2) Arlington Spy Ponders
postponed from 1/11 |
Ed Burns Arena |
| January 27, 2020 | (3) Winchester Red & Black at (0) Wakefield Warriors | Stoneham Arena |
| January 29, 2020 | (1) Westford Academy Ghosts at (1) Winchester Red & Black | O'Brien Arena |
| February 01, 2020 | (0) Lexington Minutemen at (2) Winchester Red & Black | O'Brien Arena |
| February 05, 2020 | (0) Winchester Red & Black at (2) Reading Rockets | Burbank Ice Arena |
| February 08, 2020 | (3) Belmont Marauders at (0) Winchester Red & Black | O'Brien Arena |
| February 12, 2020 | (3) Arlington Spy Ponders at (2) Winchester Red & Black | O'Brien Arena |
| February 15, 2020 | (2) Woburn Tanners at (0) Winchester Red & Black | O'Brien Arena |
| February 18, 2020 | (1) Winchester Red & Black at (3) Andover Golden Warriors
HINGHAM SHOWCASE |
Pilgrim Arena |
| February 20, 2020 | (3) Acton-Boxboro Revolution at (1) Winchester Red & Black
HINGHAM SHOWCASE |
Pilgrim Arena |
| February 25, 2020 | (2) Winchester Red & Black at (5) Bishop Fenwick Crusaders
Girls D2 Playoff |
McVann-O'Keefe Skating Rink |
| February 29, 2020 | (3) Winchester Red & Black at (4) Ursuline Academy Bears
Girls D2 Playoff |
Canton Ice House |
