| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2019 | (3) Hopkinton Hillers at (2) Medfield Warriors | Pirelli Veterans Arena |
| December 18, 2019 | (7) Hopkinton Hillers at (1) Bellingham Blackhawks | Pirelli Veterans Arena |
| December 21, 2019 | (1) Westwood Wolverines at (3) Hopkinton Hillers | New England Sports Center |
| December 28, 2019 | (1) Hudson Hawks at (6) Hopkinton Hillers | New England Sports Center |
| January 01, 2020 | (2) Algonquin Titans at (7) Hopkinton Hillers
postponed from 12-30-19 Metro West Daily News Cup |
New England Sports Center |
| January 04, 2020 | (3) Medway Mustangs at (6) Hopkinton Hillers | New England Sports Center |
| January 06, 2020 | (6) Hopkinton Hillers at (1) Ashland Clockers | New England Sports Center |
| January 08, 2020 | (8) Hopkinton Hillers at (1) Norwood Mustangs | Bajko Memorial Rink |
| January 11, 2020 | (1) Dover-Sherborn/Weston Raiders at (8) Hopkinton Hillers | New England Sports Center |
| January 15, 2020 | (4) Hopkinton Hillers at (2) Holliston Panthers | Loring Arena |
| January 22, 2020 | (2) Ashland Clockers at (7) Hopkinton Hillers | New England Sports Center |
| January 25, 2020 | (3) Medfield Warriors at (6) Hopkinton Hillers | New England Sports Center |
| January 29, 2020 | (2) Dedham Marauders at (6) Hopkinton Hillers | New England Sports Center |
| February 01, 2020 | (1) Hopkinton Hillers at (2) Westwood Wolverines | Canton Ice House |
| February 08, 2020 | (2) Norwood Mustangs at (5) Hopkinton Hillers | New England Sports Center |
| February 10, 2020 | (5) Oliver Ames Tigers at (8) Hopkinton Hillers | New England Sports Center |
| February 12, 2020 | (0) Holliston Panthers at (3) Hopkinton Hillers | New England Sports Center |
| February 15, 2020 | (4) Hopkinton Hillers at (2) Plymouth North Eagles
Fairleigh Dickenson Tournament |
Martha's Vineyard Arena |
| February 16, 2020 | (8) Hopkinton Hillers at (1) Martha's Vineyard Vineyarders
Fairleigh Dickenson Tournament |
Martha's Vineyard Arena |
| February 17, 2020 | (9) Hopkinton Hillers at (0) Norton Lancers | Foxboro Sports Center |
| February 28, 2020 | (3) Silver Lake Lakers at (5) Hopkinton Hillers
Boys D3S Playoff |
Canton Ice House |
| March 01, 2020 | (5) Bishop Stang Spartans at (2) Hopkinton Hillers
Boys D3 South Playoff |
Canton Ice House |
