| Date & Time | Game | Venue |
|---|---|---|
| December 21, 2019 | (0) Hamilton-Wenham Generals at (1) Lynnfield Pioneers | McVann-O'Keefe Skating Rink |
| December 26, 2019 | (0) Hamilton-Wenham Generals at (3) Amesbury Redhawks
Lynn Holiday Tournament |
Connery Memorial Arena |
| December 27, 2019 | (8) Hamilton-Wenham Generals at (2) Lynn Jets
Lynn Holiday Tournament |
Connery Memorial Arena |
| December 30, 2019 | (2) Pentucket Panthers at (3) Hamilton-Wenham Generals | Johnson Hockey Rink |
| January 04, 2020 | (3) Somerville Highlanders at (2) Hamilton-Wenham Generals | Johnson Hockey Rink |
| January 08, 2020 | (2) Hamilton-Wenham Generals at (0) St. Joseph Prep The Phoenix | Warrior Ice Arena |
| January 11, 2020 | (0) Revere/Malden Patriots at (4) Hamilton-Wenham Generals | Johnson Hockey Rink |
| January 15, 2020 | (1) Hamilton-Wenham Generals at (1) Essex Tech Hawks | Essex Sports Center |
| January 20, 2020 | (1) Swampscott Big Blue at (3) Hamilton-Wenham Generals | Johnson Hockey Rink |
| January 25, 2020 | (3) Bedford Bucs at (0) Hamilton-Wenham Generals | Johnson Hockey Rink |
| January 29, 2020 | (1) Hamilton-Wenham Generals at (3) Rockport Vikings | Dorothy Talbot Rink |
| February 01, 2020 | (1) Shawsheen Rams at (3) Hamilton-Wenham Generals | Johnson Hockey Rink |
| February 03, 2020 | (5) Hamilton-Wenham Generals at (1) OBryant Tigers | Matthews Arena |
| February 05, 2020 | (2) Hamilton-Wenham Generals at (4) Latin Academy Dragons | Matthews Arena |
| February 08, 2020 | (1) Essex Tech Hawks at (1) Hamilton-Wenham Generals | Johnson Hockey Rink |
| February 12, 2020 | (2) Hamilton-Wenham Generals at (0) Revere/Malden Patriots | Cronin Skating Rink |
| February 15, 2020 | (1) Rockport Vikings at (3) Hamilton-Wenham Generals | Johnson Hockey Rink |
| February 16, 2020 | (1) Hamilton-Wenham Generals at (4) Amesbury Redhawks
Newburyport Bank Ice Hockey Classic |
Graf Rink |
| February 18, 2020 | (3) Pentucket Panthers at (2) Hamilton-Wenham Generals
Newburyport Bank Ice Hockey Classic |
Graf Rink |
| February 19, 2020 | (2) OBryant Tigers at (10) Hamilton-Wenham Generals | Johnson Hockey Rink |
| February 27, 2020 | (2) Hamilton-Wenham Generals at (3) Newton South Lions
Boys D3 N Playoff |
O'Brien Arena |
