| Date & Time | Game | Venue |
|---|---|---|
| December 08, 2018 | (10) Hopkinton Hillers at (0) East Longmeadow Spartans | Olympia Center |
| December 15, 2018 | (2) Ashland Clockers at (5) Hopkinton Hillers | Navin Arena |
| December 20, 2018 | (3) Hopkinton Hillers at (6) Medfield Warriors | Pirelli Veterans Arena |
| December 22, 2018 | (1) Bellingham Blackhawks at (5) Hopkinton Hillers | New England Sports Center |
| December 26, 2018 | (4) Hopkinton Hillers at (0) Marlboro Panthers
Metro West Daily News Cup |
New England Sports Center |
| December 29, 2018 | (2) Algonquin Titans at (1) Hopkinton Hillers
Metro west Daily News Cup |
New England Sports Center |
| January 02, 2019 | (4) Hopkinton Hillers at (1) Holliston Panthers | Blackstone Valley Ice Arena |
| January 05, 2019 | (3) Hopkinton Hillers at (3) Westwood Wolverines | Canton Ice House |
| January 09, 2019 | (5) Hopkinton Hillers at (2) Medway Mustangs | Pirelli Veterans Arena |
| January 12, 2019 | (3) Norwood Mustangs at (3) Hopkinton Hillers | Navin Arena |
| January 16, 2019 | (5) Hopkinton Hillers at (0) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| January 19, 2019 | (0) Holliston Panthers at (1) Hopkinton Hillers | Navin Arena |
| January 23, 2019 | (1) Norton Lancers at (5) Hopkinton Hillers | Navin Arena |
| January 26, 2019 | (2) Hopkinton Hillers at (3) Ashland Clockers | Loring Arena |
| January 30, 2019 | (2) Medfield Warriors at (1) Hopkinton Hillers | Navin Arena |
| February 02, 2019 | (5) Hopkinton Hillers at (2) Dedham Marauders | Noble & Greenough School |
| February 06, 2019 | (4) Westwood Wolverines at (3) Hopkinton Hillers | Navin Arena |
| February 13, 2019 | (2) Hopkinton Hillers at (5) Norwood Mustangs | Bajko Memorial Rink |
| February 16, 2019 | (5) Hopkinton Hillers at (1) Plymouth North Eagles
FAIRLEIGH Dickinson Tournament |
Martha's Vineyard Arena |
| February 17, 2019 | (7) Hopkinton Hillers at (3) Martha's Vineyard Vineyarders
fairleigh Dickinson Tournament |
Martha's Vineyard Arena |
| February 28, 2019 | (4) Hopkinton Hillers at (0) Bishop Stang Spartans | Canton Ice House |
| March 03, 2019 | (3) Hopkinton Hillers at (0) North Quincy / Quincy Red Raiders | Gallo Arena |
| March 07, 2019 | (7) Hopkinton Hillers at (0) Coyle & Cassidy Warriors | Gallo Arena |
| March 10, 2019 | (6) Hopkinton Hillers at (2) Ashland Clockers | Gallo Arena |
| March 13, 2019 | (8) Hopkinton Hillers at (3) Lowell Red Raiders | Tsongas Center |
| March 17, 2019 | (3) Wachusett Mountaineers at (2) Hopkinton Hillers | TD Garden |
