| Date & Time | Game | Venue |
|---|---|---|
| December 09, 2023 | (1) Hopkinton Hillers at (0) King Philip Warriors | Foxboro Sports Center |
| December 11, 2023 | (5) Hopkinton Hillers at (0) Holliston Panthers | New England Sports Center |
| December 16, 2023 | (3) Ashland Clockers at (3) Hopkinton Hillers
OT game ends in a tie |
New England Sports Center |
| December 20, 2023 | (7) Hopkinton Hillers at (4) Westwood Wolverines | Canton Ice House |
| December 27, 2023 | (4) Algonquin Titans at (5) Hopkinton Hillers | New England Sports Center |
| December 30, 2023 | (0) Hopkinton Hillers at (3) Marlboro Panthers | New England Sports Center |
| January 03, 2024 | (2) Medfield Warriors at (4) Hopkinton Hillers | New England Sports Center |
| January 06, 2024 | (3) Hopkinton Hillers at (3) Norwood Mustangs
OT game ends in a tie |
The Skating Club of Boston |
| January 10, 2024 | (2) Bellingham Blackhawks at (10) Hopkinton Hillers | New England Sports Center |
| January 12, 2024 | (3) Hopkinton Hillers at (2) Norton Lancers | Foxboro Sports Center |
| January 20, 2024 | (3) Hopkinton Hillers at (1) Medway Mustangs | Pirelli Veterans Arena |
| January 24, 2024 | (4) Dover-Sherborn/Weston Raiders at (2) Hopkinton Hillers | New England Sports Center |
| January 27, 2024 | (2) Hopkinton Hillers at (1) Dedham Marauders | Bliss Omni and Flood Rink |
| January 31, 2024 | (2) Holliston Panthers at (5) Hopkinton Hillers | New England Sports Center |
| February 03, 2024 | (2) Hopkinton Hillers at (1) Ashland Clockers | Loring Arena |
| February 07, 2024 | (0) Westwood Wolverines at (2) Hopkinton Hillers | New England Sports Center |
| February 11, 2024 | (3) Hopkinton Hillers at (5) Medfield Warriors | Rodman Arena |
| February 14, 2024 | (1) Norwood Mustangs at (2) Hopkinton Hillers | New England Sports Center |
| February 17, 2024 | (5) Hopkinton Hillers at (4) Martha's Vineyard Vineyarders
Falleigh Dickinson Tournamant |
Martha's Vineyard Arena |
| February 18, 2024 | (2) Hopkinton Hillers at (7) Lynnfield Pioneers
Farleigh Dickinson Tournament Championship Game |
Martha's Vineyard Arena |
| February 28, 2024 | (4) Hopkinton Hillers at (5) Masconomet Chieftains
MIAA D2 BOYS STATE TOURNAMENT - Round 32 (overtime) |
Haverhill Valley Forum |
