| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (2) Triton Vikings at (2) Lynnfield Pioneers | McVann-O'Keefe Skating Rink |
| December 18, 2019 | (2) Masconomet Chieftains at (1) Lynnfield Pioneers | McVann-O'Keefe Skating Rink |
| December 21, 2019 | (0) Hamilton-Wenham Generals at (1) Lynnfield Pioneers | McVann-O'Keefe Skating Rink |
| December 26, 2019 | (4) Lynnfield Pioneers at (1) Danvers Falcons
Castle Island Tournament |
Murphy Memorial Rink |
| December 27, 2019 | (2) Latin Academy Dragons at (6) Lynnfield Pioneers
Castle Island Tournament |
Murphy Memorial Rink |
| December 30, 2019 | (1) Lynnfield Pioneers at (4) Medfield Warriors | Pirelli Veterans Arena |
| January 04, 2020 | (4) Lynnfield Pioneers at (1) Pentucket Panthers | Veterans Memorial Ice Rink |
| January 09, 2020 | (0) Lynnfield Pioneers at (3) Amesbury Redhawks | Graf Rink |
| January 11, 2020 | (4) Westwood Wolverines at (11) Lynnfield Pioneers | McVann-O'Keefe Skating Rink |
| January 15, 2020 | (0) Newburyport Clippers at (5) Lynnfield Pioneers | McVann-O'Keefe Skating Rink |
| January 18, 2020 | (0) North Reading Hornets at (0) Lynnfield Pioneers | McVann-O'Keefe Skating Rink |
| January 22, 2020 | (4) Lynnfield Pioneers at (7) Triton Vikings | Graf Rink |
| January 25, 2020 | (2) Lynnfield Pioneers at (8) Masconomet Chieftains | Warrior Ice Arena |
| January 29, 2020 | (2) Pentucket Panthers at (5) Lynnfield Pioneers | McVann-O'Keefe Skating Rink |
| February 01, 2020 | (1) Amesbury Redhawks at (3) Lynnfield Pioneers | McVann-O'Keefe Skating Rink |
| February 05, 2020 | (0) Saugus Sachems at (6) Lynnfield Pioneers
Senior Night |
McVann-O'Keefe Skating Rink |
| February 07, 2020 | (2) Lynnfield Pioneers at (5) Newburyport Clippers | Graf Rink |
| February 12, 2020 | (4) Lynnfield Pioneers at (1) North Reading Hornets | Kasabuski Arena |
| February 19, 2020 | (3) Lynnfield Pioneers at (4) Gloucester Fishermen | Dorothy Talbot Rink |
| February 25, 2020 | (2) Lynnfield Pioneers at (5) North Andover Scarlet Knights
Boys D2 N Playoff |
O'Brien Arena |
