| Date & Time | Game | Venue |
|---|---|---|
| December 18, 2019 | (10) Lincoln-Sudbury Warriors at (2) Haverhill Hillies | Veterans Memorial Ice Rink |
| December 21, 2019 | (2) Concord-Carlisle Patriots at (5) Haverhill Hillies | Veterans Memorial Ice Rink |
| December 23, 2019 | (2) Westboro Rangers at (7) Haverhill Hillies | Veterans Memorial Ice Rink |
| December 27, 2019 | (0) Shawsheen Rams at (4) Haverhill Hillies
Hillies Christmas Tournament |
Veterans Memorial Ice Rink |
| January 04, 2020 | (1) Haverhill Hillies at (4) North Andover Scarlet Knights | Brooks School Rink |
| January 08, 2020 | (4) Lowell Red Raiders at (2) Haverhill Hillies
Rivalry Game |
Veterans Memorial Ice Rink |
| January 11, 2020 | (5) Boston Latin Wolfpack at (1) Haverhill Hillies | Veterans Memorial Ice Rink |
| January 15, 2020 | (5) Haverhill Hillies at (5) Dracut/Tyngsboro Middies | Salem Ice Center |
| January 18, 2020 | (6) Tewksbury Redmen at (1) Haverhill Hillies | Veterans Memorial Ice Rink |
| January 22, 2020 | (4) Acton-Boxboro Revolution at (4) Haverhill Hillies | Haverhill Valley Forum |
| January 25, 2020 | (2) Haverhill Hillies at (7) Lincoln-Sudbury Warriors | New England Sports Center |
| January 29, 2020 | (3) Haverhill Hillies at (6) Concord-Carlisle Patriots | Edge Sports Center |
| February 01, 2020 | (7) Haverhill Hillies at (3) St. Joseph Prep The Phoenix | Warrior Ice Arena |
| February 05, 2020 | (6) North Andover Scarlet Knights at (2) Haverhill Hillies | Veterans Memorial Ice Rink |
| February 09, 2020 | (1) Haverhill Hillies at (4) Lowell Red Raiders
Rivalry Game |
Tsongas Center |
| February 12, 2020 | (1) Haverhill Hillies at (7) Boston Latin Wolfpack | Murphy Memorial Rink |
| February 14, 2020 | (3) Dracut/Tyngsboro Middies at (6) Haverhill Hillies | Veterans Memorial Ice Rink |
| February 16, 2020 | (5) Haverhill Hillies at (4) Pentucket Panthers
Newburyport Bank Ice Hockey Classic |
Graf Rink |
| February 18, 2020 | (6) Amesbury Redhawks at (2) Haverhill Hillies
Newburyport Bank Ice Hockey Classic |
Graf Rink |
| February 19, 2020 | (0) Haverhill Hillies at (5) Tewksbury Redmen | Breakaway Ice Center |
