| Date & Time | Game | Venue |
|---|---|---|
| January 16, 2021 | (2) Beverly Panthers at (7) Masconomet Chieftains | Haverhill Valley Forum |
| January 18, 2021 | (1) Saugus Sachems at (8) Masconomet Chieftains | Haverhill Valley Forum |
| January 20, 2021 | (8) Masconomet Chieftains at (1) Peabody/Salem Tanners | McVann-O'Keefe Skating Rink |
| January 27, 2021 | (2) Winthrop Vikings at (0) Masconomet Chieftains | Essex Sports Center |
| January 30, 2021 | (4) Masconomet Chieftains at (1) Gloucester Fishermen | Dorothy Talbot Rink |
| January 31, 2021 | (7) Masconomet Chieftains at (1) Swampscott Big Blue
make up date TBA |
Kasabuski Arena |
| February 03, 2021 | (6) Marblehead Magicians at (4) Masconomet Chieftains | Essex Sports Center |
| Feb. 6 Postponed | Gloucester Fishermen at Masconomet Chieftains | Haverhill Valley Forum |
| February 08, 2021 | (3) Masconomet Chieftains at (0) Danvers Falcons | Dorothy Talbot Rink |
| February 10, 2021 | (2) Danvers Falcons at (4) Masconomet Chieftains | Haverhill Valley Forum |
| February 13, 2021 | (3) Masconomet Chieftains at (3) Winthrop Vikings | Larsen Rink |
| February 17, 2021 | (0) Beverly Panthers at (3) Masconomet Chieftains | Essex Sports Center |
| February 17, 2021 | (0) Beverly Panthers at (3) Masconomet Chieftains
Bob Driscoll "Can Do" Classic |
Essex Sports Center |
| February 20, 2021 | (3) Marblehead Magicians at (6) Masconomet Chieftains | Essex Sports Center |
