| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (3) Somerville Highlanders at (8) Medford Mustangs | LoConte Rink |
| December 18, 2019 | (3) Revere/Malden Patriots at (5) Somerville Highlanders | Veterans Memorial Rink |
| December 21, 2019 | (4) Somerville Highlanders at (2) Swampscott Big Blue | Rockett Arena |
| December 26, 2019 | (1) Somerville Highlanders at (4) Cambridge Rindge & Latin Falcons
Rivalry Game |
Simoni Skating Rink |
| December 27, 2019 | (1) Somerville Highlanders at (1) Revere/Malden Patriots
FIRST RESPONDER CUP HOLIDAY TOURNAMENT |
Simoni Skating Rink |
| January 01, 2020 | (9) Somerville Highlanders at (1) Lynn Jets | Connery Memorial Arena |
| January 04, 2020 | (3) Somerville Highlanders at (2) Hamilton-Wenham Generals | Johnson Hockey Rink |
| January 08, 2020 | (3) Somerville Highlanders at (3) Latin Academy Dragons | Matthews Arena |
| January 11, 2020 | (3) Lynn Jets at (9) Somerville Highlanders | Veterans Memorial Rink |
| January 15, 2020 | (4) Somerville Highlanders at (1) Everett Crimson Tide | Allied Veterans Rink |
| January 18, 2020 | (2) Somerville Highlanders at (5) Watertown/Wayland Raiders | John A. Ryan Arena |
| January 27, 2020 | (4) Somerville Highlanders at (6) Northeast Tech Golden Knights | Valley Forum II |
| January 29, 2020 | (3) Somerville Highlanders at (5) St. Joseph Prep The Phoenix | Warrior Ice Arena |
| February 01, 2020 | (5) Swampscott Big Blue at (6) Somerville Highlanders | Veterans Memorial Rink |
| February 05, 2020 | (1) Somerville Highlanders at (1) Revere/Malden Patriots | Cronin Skating Rink |
| February 08, 2020 | (3) St. Joseph Prep The Phoenix at (4) Somerville Highlanders | Veterans Memorial Rink |
| February 12, 2020 | (2) Medford Mustangs at (3) Somerville Highlanders | Veterans Memorial Rink |
| February 15, 2020 | (1) Latin Academy Dragons at (0) Somerville Highlanders | Veterans Memorial Rink |
| February 17, 2020 | (6) Somerville Highlanders at (2) Everett Crimson Tide
Mulloy Tournament |
Allied Veterans Rink |
| February 19, 2020 | (2) Essex Tech Hawks at (0) Somerville Highlanders
Malloy Tournament Championship |
Allied Veterans Rink |
| February 27, 2020 | (5) Lowell Red Raiders at (0) Somerville Highlanders
Boys D3 N Playoffs |
Stoneham Arena |
