| Date & Time | Game | Venue |
|---|---|---|
| December 08, 2018 | (4) Gloucester Fishermen at (1) Lynnfield Pioneers | McVann-O'Keefe Skating Rink |
| December 12, 2018 | (4) Lynnfield Pioneers at (2) Masconomet Chieftains | Haverhill Valley Forum |
| December 15, 2018 | (4) Pentucket Panthers at (4) Lynnfield Pioneers | McVann-O'Keefe Skating Rink |
| December 22, 2018 | (3) Lynnfield Pioneers at (2) Hamilton-Wenham Generals | Johnson Hockey Rink |
| December 26, 2018 | (1) Watertown/Wayland Raiders at (4) Lynnfield Pioneers
WOLFPACK HOLIDAY TOURNAMENT |
Murphy Memorial Rink |
| December 27, 2018 | (1) Lynnfield Pioneers at (2) Boston Latin Wolfpack
CASTLE ISLAND CHRISTMAS TOURNAMENT |
Murphy Memorial Rink |
| December 29, 2018 | (5) Lynnfield Pioneers at (1) Peabody/Salem Tanners | McVann-O'Keefe Skating Rink |
| January 02, 2019 | (6) Masconomet Chieftains at (3) Lynnfield Pioneers | McVann-O'Keefe Skating Rink |
| January 05, 2019 | (0) Amesbury Redhawks at (3) Lynnfield Pioneers | McVann-O'Keefe Skating Rink |
| January 12, 2019 | (1) Lynnfield Pioneers at (1) Newburyport Clippers | Graf Rink |
| January 15, 2019 | (7) Lynnfield Pioneers at (2) North Reading Hornets | Kasabuski Arena |
| January 19, 2019 | (3) Lynnfield Pioneers at (4) Triton Vikings | Graf Rink |
| January 26, 2019 | (4) Lynnfield Pioneers at (1) Pentucket Panthers | Veterans Memorial Ice Rink |
| January 30, 2019 | (5) Lynnfield Pioneers at (3) Amesbury Redhawks | Haverhill Valley Forum |
| February 02, 2019 | (4) Medfield Warriors at (5) Lynnfield Pioneers | McVann-O'Keefe Skating Rink |
| February 06, 2019 | (4) Newburyport Clippers at (5) Lynnfield Pioneers | McVann-O'Keefe Skating Rink |
| February 09, 2019 | (3) Triton Vikings at (3) Lynnfield Pioneers | McVann-O'Keefe Skating Rink |
| February 13, 2019 | (0) North Reading Hornets at (4) Lynnfield Pioneers | McVann-O'Keefe Skating Rink |
| February 16, 2019 | (0) Lynnfield Pioneers at (0) Westwood Wolverines | Canton Ice House |
| February 20, 2019 | (0) Lynnfield Pioneers at (4) Gloucester Fishermen | Dorothy Talbot Rink |
| February 26, 2019 | (1) Lynnfield Pioneers at (2) Tewksbury Redmen | Chelmsford Forum |
