| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2018 | (4) Lynnfield Pioneers at (2) Masconomet Chieftains | Haverhill Valley Forum |
| December 15, 2018 | (3) Masconomet Chieftains at (0) Amesbury Redhawks | Haverhill Valley Forum |
| December 22, 2018 | (4) Masconomet Chieftains at (1) Gloucester Fishermen | Dorothy Talbot Rink |
| December 26, 2018 | (0) Plymouth South Panthers at (7) Masconomet Chieftains
STONEHAM HOLIDAY CLASSIC CHAMPIONSHIP |
Stoneham Arena |
| December 29, 2018 | (0) Stoneham Spartans at (3) Masconomet Chieftains
STONEHAM HOLIDAY CLASSIC CHAMPIONSHIP |
Stoneham Arena |
| January 02, 2019 | (6) Masconomet Chieftains at (3) Lynnfield Pioneers | McVann-O'Keefe Skating Rink |
| January 05, 2019 | (3) Masconomet Chieftains at (1) Triton Vikings | Graf Rink |
| January 09, 2019 | (2) Pentucket Panthers at (10) Masconomet Chieftains | Valley Forum II |
| January 12, 2019 | (1) North Reading Hornets at (5) Masconomet Chieftains | Veterans Memorial Ice Rink |
| January 19, 2019 | (0) Newburyport Clippers at (2) Masconomet Chieftains | Veterans Memorial Ice Rink |
| January 21, 2019 | (0) Beverly Panthers at (6) Masconomet Chieftains | Haverhill Valley Forum |
| January 26, 2019 | (1) Amesbury Redhawks at (3) Masconomet Chieftains | Veterans Memorial Ice Rink |
| January 30, 2019 | (2) Triton Vikings at (3) Masconomet Chieftains | Veterans Memorial Ice Rink |
| February 02, 2019 | (9) Masconomet Chieftains at (0) Pentucket Panthers | Veterans Memorial Ice Rink |
| February 06, 2019 | (4) Masconomet Chieftains at (2) North Reading Hornets | Kasabuski Arena |
| February 09, 2019 | (5) Masconomet Chieftains at (1) Newburyport Clippers | Graf Rink |
| February 13, 2019 | (4) Masconomet Chieftains at (2) Westford Academy Ghosts | Skate 3 |
| February 16, 2019 | (1) Peabody/Salem Tanners at (11) Masconomet Chieftains
BOB DRISCOLL CAN DO CLASSIC |
Lawrence Valley Forum |
| February 18, 2019 | (0) Masconomet Chieftains at (2) Danvers Falcons | Raymond J. Bourque Arena |
| February 22, 2019 | (4) Masconomet Chieftains at (2) Melrose Red Hawks | Kasabuski Arena |
| February 27, 2019 | (2) Wilmington Wildcats at (5) Masconomet Chieftains | O'Brien Arena |
| March 01, 2019 | (5) Triton Vikings at (1) Masconomet Chieftains | Stoneham Arena |
