| Date & Time | Game | Venue |
|---|---|---|
| December 08, 2018 | (12) Masconomet Chieftains at (1) Beverly/Danvers/Ipswich Panthers | Raymond J. Bourque Arena |
| December 15, 2018 | (2) Masconomet Chieftains at (2) Peabody/Lynnfield/North Reading Tanners | McVann-O'Keefe Skating Rink |
| December 26, 2018 | (1) Medford/Malden Mustangs at (1) Masconomet Chieftains | Haverhill Valley Forum |
| December 28, 2018 | (2) Masconomet Chieftains at (3) Melrose Red Hawks | Flynn Memorial Rink |
| December 29, 2018 | (6) Masconomet Chieftains at (0) Marblehead Magicians | Rockett Arena |
| January 02, 2019 | (5) Andover Golden Warriors at (2) Masconomet Chieftains | Haverhill Valley Forum |
| January 05, 2019 | (2) Masconomet Chieftains at (1) Winthrop Vikings | Larsen Rink |
| January 10, 2019 | (0) Exeter (N.H.) at (9) Masconomet Chieftains | Haverhill Valley Forum |
| January 12, 2019 | (1) Masconomet Chieftains at (2) Andover Golden Warriors | Breakaway Ice Center |
| January 16, 2019 | (0) Beverly/Danvers/Ipswich Panthers at (6) Masconomet Chieftains | Haverhill Valley Forum |
| January 26, 2019 | (0) Falmouth (Maine) at (7) Masconomet Chieftains | Haverhill Valley Forum |
| January 30, 2019 | (1) HPNA Hillies at (3) Masconomet Chieftains
location and time updated per coach ryan sugar |
Lawrence Valley Forum |
| February 02, 2019 | (6) Masconomet Chieftains at (1) Medford/Malden Mustangs | LoConte Rink |
| February 03, 2019 | (2) Longmeadow Lancers at (1) Masconomet Chieftains
make up date TBA |
Haverhill Valley Forum |
| February 06, 2019 | (2) Marblehead Magicians at (6) Masconomet Chieftains | Haverhill Valley Forum |
| February 09, 2019 | (2) Peabody/Lynnfield/North Reading Tanners at (3) Masconomet Chieftains | Lawrence Valley Forum |
| February 13, 2019 | (5) Winthrop Vikings at (3) Masconomet Chieftains | Haverhill Valley Forum |
| February 16, 2019 | (5) Shrewsbury Colonials at (2) Masconomet Chieftains | Lawrence Valley Forum |
| February 19, 2019 | (3) Billerica/Chelmsford Indians at (5) Masconomet Chieftains
NEWBURYPORT BANK CLASSIC |
Graf Rink |
| February 21, 2019 | (3) Tewksbury/Methuen Red Rangers at (0) Masconomet Chieftains
NEWBURYPORT BANK CLASSIC championship |
Graf Rink |
| February 27, 2019 | (5) Masconomet Chieftains at (1) Melrose Red Hawks | Flynn Memorial Rink |
| March 02, 2019 | (1) Masconomet Chieftains at (6) Longmeadow Lancers | John A. Ryan Arena |
