| Date & Time | Game | Venue |
|---|---|---|
| December 18, 2019 | (2) Burlington Red Devils at (1) Winchester Red & Black | O'Brien Arena |
| December 21, 2019 | (2) Wilmington Wildcats at (1) Winchester Red & Black | O'Brien Arena |
| December 23, 2019 | (7) Lincoln-Sudbury Warriors at (5) Winchester Red & Black | O'Brien Arena |
| December 31, 2019 | (2) Winchester Red & Black at (2) Lexington Minutemen | Hayden Ice Facility |
| January 04, 2020 | (0) Reading Rockets at (4) Winchester Red & Black | O'Brien Arena |
| January 08, 2020 | (3) Belmont Marauders at (0) Winchester Red & Black | O'Brien Arena |
| January 12, 2020 | (2) Winchester Red & Black at (3) Arlington Spy Ponders
postponed from 1/11 |
Ed Burns Arena |
| January 14, 2020 | (3) Winchester Red & Black at (3) Woburn Tanners | O'Brien Arena |
| January 18, 2020 | (6) Winchester Red & Black at (1) Stoneham Spartans | Stoneham Arena |
| January 20, 2020 | (2) Winchester Red & Black at (3) BC High Eagles | Clark Athletic Center |
| January 22, 2020 | (0) St. Mary's Lynn Spartans at (3) Winchester Red & Black | O'Brien Arena |
| January 25, 2020 | (3) Melrose Red Hawks at (2) Winchester Red & Black | O'Brien Arena |
| January 29, 2020 | (1) Winchester Red & Black at (3) Wakefield Warriors | Stoneham Arena |
| February 01, 2020 | (2) Lexington Minutemen at (2) Winchester Red & Black | O'Brien Arena |
| February 03, 2020 | (2) Austin Prep Cougars at (2) Winchester Red & Black | O'Brien Arena |
| February 05, 2020 | (1) Winchester Red & Black at (4) Reading Rockets | Burbank Ice Arena |
| February 08, 2020 | (1) Winchester Red & Black at (1) Belmont Marauders | Skip Viglirolo Rink |
| February 12, 2020 | (3) Arlington Spy Ponders at (2) Winchester Red & Black | O'Brien Arena |
| February 15, 2020 | (1) Woburn Tanners at (3) Winchester Red & Black | O'Brien Arena |
| February 17, 2020 | (3) Winchester Red & Black at (1) Saint John's Shrewsbury Pioneers
Newburyport Tourney |
Graf Rink |
| February 19, 2020 | (8) Winchester Red & Black at (3) Newburyport Clippers
Newburyport Tournament |
Graf Rink |
