| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (4) Masconomet Chieftains at (1) Gloucester Fishermen
Blaf "9" Memorial Game |
Dorothy Talbot Rink |
| December 18, 2019 | (2) Masconomet Chieftains at (1) Lynnfield Pioneers | McVann-O'Keefe Skating Rink |
| December 21, 2019 | (0) Masconomet Chieftains at (3) Canton Bulldogs | Canton Ice House |
| December 23, 2019 | (7) Masconomet Chieftains at (1) Groton-Dunstable Crusaders
JL11 Holiday Classic |
Stoneham Arena |
| December 26, 2019 | (2) Masconomet Chieftains at (3) Stoneham Spartans
Stoneham Holiday Classic |
Stoneham Arena |
| December 28, 2019 | (4) Masconomet Chieftains at (1) Newburyport Clippers | Graf Rink |
| January 04, 2020 | (0) Amesbury Redhawks at (6) Masconomet Chieftains | Haverhill Valley Forum |
| January 08, 2020 | (1) Triton Vikings at (4) Masconomet Chieftains | Haverhill Valley Forum |
| January 11, 2020 | (4) Masconomet Chieftains at (1) Pentucket Panthers | Veterans Memorial Ice Rink |
| January 15, 2020 | (5) Masconomet Chieftains at (0) North Reading Hornets | Kasabuski Arena |
| January 20, 2020 | (5) Masconomet Chieftains at (2) Beverly Panthers | Raymond J. Bourque Arena |
| January 25, 2020 | (2) Lynnfield Pioneers at (8) Masconomet Chieftains | Warrior Ice Arena |
| January 27, 2020 | (2) Newburyport Clippers at (2) Masconomet Chieftains | Haverhill Valley Forum |
| January 29, 2020 | (4) Masconomet Chieftains at (1) Amesbury Redhawks | Lawrence Valley Forum |
| February 01, 2020 | (3) Masconomet Chieftains at (1) Triton Vikings | Graf Rink |
| February 05, 2020 | (0) Pentucket Panthers at (7) Masconomet Chieftains | Haverhill Valley Forum |
| February 08, 2020 | (3) North Reading Hornets at (4) Masconomet Chieftains
Senior Night |
Haverhill Valley Forum |
| February 12, 2020 | (1) Westford Academy Ghosts at (3) Masconomet Chieftains | Haverhill Valley Forum |
| February 17, 2020 | (1) Danvers Falcons at (2) Masconomet Chieftains
Bob Driscoll "Can Do" Classic |
Essex Sports Center |
| February 20, 2020 | (3) Masconomet Chieftains at (4) Melrose Red Hawks | Stoneham Arena |
| February 25, 2020 | (0) Stoneham Spartans at (2) Masconomet Chieftains
Boys D2 N Playoff |
O'Brien Arena |
| February 28, 2020 | (2) Boston Latin Wolfpack at (3) Masconomet Chieftains
Boys D2 N Playoff |
Chelmsford Forum |
| March 03, 2020 | (2) Triton Vikings at (1) Masconomet Chieftains
Boys D2 N Playoff |
Chelmsford Forum |
