| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (4) Hopedale / Milford Blue Raiders at (4) Assabet Aztecs | Navin Arena |
| December 18, 2019 | (3) Hopedale / Milford Blue Raiders at (0) Grafton Gators | Buffone Arena |
| December 21, 2019 | (3) Hopedale / Milford Blue Raiders at (5) Dover-Sherborn/Weston Raiders
St. Joseph Prep Holiday Tourney |
Warrior Ice Arena |
| December 23, 2019 | (8) Hopedale / Milford Blue Raiders at (0) St. Joseph Prep The Phoenix
ST JOSEPH PREP HOLDIAY TOURNAMENT |
Warrior Ice Arena |
| December 28, 2019 | (4) Littleton/Bromfield Tigers at (3) Hopedale / Milford Blue Raiders | Blackstone Valley Ice Arena |
| January 04, 2020 | (6) Hopedale / Milford Blue Raiders at (1) Ludlow / Belchertown Lions | Olympia Center |
| January 06, 2020 | (2) Hopedale / Milford Blue Raiders at (4) Northbridge Rams | New England Sports Center |
| January 08, 2020 | (3) Hopedale / Milford Blue Raiders at (3) Littleton/Bromfield Tigers | Groton School Rink |
| January 11, 2020 | (7) Hopedale / Milford Blue Raiders at (1) Gardner/Murdock Wildcats | Gardner Veterans Skating Rink |
| January 14, 2020 | (0) Fitchburg Red Raiders at (10) Hopedale / Milford Blue Raiders | Wallace Civic Center |
| January 18, 2020 | (0) St. Peter Marian Guardians at (13) Hopedale / Milford Blue Raiders | Blackstone Valley Ice Arena |
| January 20, 2020 | (2) Oakmont/Narragansett Spartans at (2) Hopedale / Milford Blue Raiders | Blackstone Valley Ice Arena |
| January 25, 2020 | (3) Watertown/Wayland Raiders at (6) Hopedale / Milford Blue Raiders | Blackstone Valley Ice Arena |
| January 29, 2020 | (1) Lunenburg/Ayer-Shirley Blue Knights at (5) Hopedale / Milford Blue Raiders | Blackstone Valley Ice Arena |
| February 01, 2020 | (2) East Longmeadow Spartans at (6) Hopedale / Milford Blue Raiders | Blackstone Valley Ice Arena |
| February 05, 2020 | (1) Hopedale / Milford Blue Raiders at (1) Worcester/Leicester Wildcats | Buffone Arena |
| February 08, 2020 | (5) Northbridge Rams at (3) Hopedale / Milford Blue Raiders | Blackstone Valley Ice Arena |
| February 12, 2020 | (2) Grafton Gators at (3) Hopedale / Milford Blue Raiders | Blackstone Valley Ice Arena |
| February 15, 2020 | (6) Assabet Aztecs at (5) Hopedale / Milford Blue Raiders | Blackstone Valley Ice Arena |
| February 19, 2020 | (2) Worcester/Leicester Wildcats at (2) Hopedale / Milford Blue Raiders | Blackstone Valley Ice Arena |
| February 26, 2020 | (2) Oakmont/Narragansett Spartans at (3) Hopedale / Milford Blue Raiders
Boys D3A Central Playoff |
Horgan Skating Arena |
| March 01, 2020 | (1) Grafton Gators at (4) Hopedale / Milford Blue Raiders
Boys D3A Central Playoff |
Wallace Civic Center |
| March 04, 2020 | (2) Hopedale / Milford Blue Raiders at (4) Lunenburg/Ayer-Shirley Blue Knights
Boys D3A Central Final |
Wallace Civic Center |
