| Date & Time | Game | Venue |
|---|---|---|
| January 09, 2021 | (3) Masconomet Chieftains at (5) Peabody/Lynnfield/North Reading Tanners | McVann-O'Keefe Skating Rink |
| January 16, 2021 | (4) Gloucester Fishermen at (4) Masconomet Chieftains | Haverhill Valley Forum |
| January 18, 2021 | (3) Masconomet Chieftains at (2) Newburyport Clippers | Graf Rink |
| January 21, 2021 | (1) Masconomet Chieftains at (2) Medford/Malden Mustangs | LoConte Rink |
| Jan. 23 Postponed | Marblehead Magicians at Masconomet Chieftains | Haverhill Valley Forum |
| January 27, 2021 | (6) Winthrop Vikings at (8) Masconomet Chieftains | Haverhill Valley Forum |
| January 30, 2021 | (5) Newburyport Clippers at (1) Masconomet Chieftains | Haverhill Valley Forum |
| February 03, 2021 | (2) Masconomet Chieftains at (5) Gloucester (W) | Dorothy Talbot Rink |
| Feb. 3 Postponed | Peabody/Lynnfield/North Reading Tanners at Masconomet Chieftains | Haverhill Valley Forum |
| February 06, 2021 | (6) Beverly/Danvers/Ipswich Panthers at (1) Masconomet Chieftains | Haverhill Valley Forum |
| February 07, 2021 | (2) Beverly/Danvers/Ipswich Panthers at (4) Masconomet Chieftains | Haverhill Valley Forum |
| February 10, 2021 | (4) Masconomet Chieftains at (6) Gloucester Fishermen | Dorothy Talbot Rink |
| February 12, 2021 | (1) Masconomet Chieftains at (2) Marblehead Magicians
GAME ADDED (MHS) |
Cronin Skating Rink |
| February 13, 2021 | (4) Medford/Malden Mustangs at (2) Masconomet Chieftains | Haverhill Valley Forum |
| February 16, 2021 | (2) Peabody/Lynnfield/North Reading Tanners at (1) Masconomet Chieftains | Haverhill Valley Forum |
| February 17, 2021 | (7) Marblehead Magicians at (2) Masconomet Chieftains | Haverhill Valley Forum |
| February 20, 2021 | (1) Masconomet Chieftains at (3) Winthrop Vikings | Larsen Rink |
