| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2019 | (1) Dedham Marauders at (1) Winthrop Vikings | Larsen Rink |
| December 14, 2019 | (1) Winthrop Vikings at (4) Beverly Panthers | Raymond J. Bourque Arena |
| December 18, 2019 | (11) Winthrop Vikings at (1) Lynn Jets | Connery Memorial Arena |
| December 21, 2019 | (2) Winthrop Vikings at (2) Mansfield Hornets | Foxboro Sports Center |
| December 26, 2019 | (0) Oliver Ames Tigers at (3) Winthrop Vikings | Larsen Rink |
| December 28, 2019 | (0) Portland (ME) at (3) Winthrop Vikings | Larsen Rink |
| December 31, 2019 | (0) Saugus Sachems at (5) Winthrop Vikings | Larsen Rink |
| January 04, 2020 | (3) Gloucester Fishermen at (1) Winthrop Vikings | Larsen Rink |
| January 08, 2020 | (5) Cambridge Rindge & Latin Falcons at (2) Winthrop Vikings | Larsen Rink |
| January 11, 2020 | (3) Winthrop Vikings at (2) Bishop Fenwick Crusaders | McVann-O'Keefe Skating Rink |
| January 15, 2020 | (3) Marblehead Magicians at (3) Winthrop Vikings | Larsen Rink |
| January 18, 2020 | (2) Winthrop Vikings at (0) Swampscott Big Blue | Rockett Arena |
| January 22, 2020 | (2) Winthrop Vikings at (4) Danvers Falcons | Raymond J. Bourque Arena |
| January 25, 2020 | (2) Beverly Panthers at (1) Winthrop Vikings | Larsen Rink |
| January 29, 2020 | (0) Winthrop Vikings at (4) Gloucester Fishermen | Dorothy Talbot Rink |
| February 01, 2020 | (1) Mansfield Hornets at (6) Winthrop Vikings | Larsen Rink |
| February 08, 2020 | (1) Winthrop Vikings at (4) Marblehead Magicians | Rockett Arena |
| February 12, 2020 | (4) Winthrop Vikings at (1) Peabody/Salem Tanners | McVann-O'Keefe Skating Rink |
| February 15, 2020 | (2) Danvers Falcons at (1) Winthrop Vikings | Larsen Rink |
| February 19, 2020 | (5) Winthrop Vikings at (1) Saugus Sachems | Kasabuski Arena |
| February 25, 2020 | (0) Winthrop Vikings at (1) Triton Vikings
Boys D2 N Playoff |
Stoneham Arena |
