| Date & Time | Game | Venue |
|---|---|---|
| December 08, 2021 | Fitchburg / Monty Tech Red Raiders at Hamilton-Wenham Generals | PINGREE SCHOOL |
| December 16, 2021 | (1) Everett Crimson Tide at (6) Hamilton-Wenham Generals | Raymond J. Bourque Arena |
| December 18, 2021 | (6) North Reading Hornets at (2) Hamilton-Wenham Generals | Raymond J. Bourque Arena |
| December 22, 2021 | (1) Hamilton-Wenham Generals at (5) Essex Tech Hawks | Essex Sports Center |
| December 27, 2021 | (5) Hamilton-Wenham Generals at (2) Rockport Vikings
Lynn Holiday Tournament |
Connery Memorial Arena |
| December 28, 2021 | (3) Hamilton-Wenham Generals at (2) Swampscott Big Blue
Christmas Tourney Finals ( Loss OT) |
Connery Memorial Arena |
| Jan. 6 Postponed | Northeast Tech Golden Knights at Hamilton-Wenham Generals
make-up TBA |
Raymond J. Bourque Arena |
| January 08, 2022 | (5) Lynnfield Pioneers at (1) Hamilton-Wenham Generals | PINGREE SCHOOL |
| January 12, 2022 | (4) Hamilton-Wenham Generals at (2) Pentucket Panthers | Veterans Memorial Ice Rink |
| January 17, 2022 | (0) Swampscott Big Blue at (4) Hamilton-Wenham Generals | Johnson Hockey Rink |
| January 20, 2022 | (2) Hamilton-Wenham Generals at (4) Shawsheen Rams | Hallenborg Memorial Pavilion |
| January 23, 2022 | (4) Northeast Tech Golden Knights at (3) Hamilton-Wenham Generals | PINGREE SCHOOL |
| January 30, 2022 | (0) Lynn Jets at (11) Hamilton-Wenham Generals | PINGREE SCHOOL |
| February 05, 2022 | (1) Pentucket Panthers at (3) Hamilton-Wenham Generals | PINGREE SCHOOL |
| February 09, 2022 | (3) Hamilton-Wenham Generals at (4) Bedford Bucs | Edge Sports Center |
| February 12, 2022 | (5) Essex Tech Hawks at (0) Hamilton-Wenham Generals | PINGREE SCHOOL |
| February 14, 2022 | (10) Hamilton-Wenham Generals at (2) Everett Crimson Tide | Allied Veterans Rink |
| February 16, 2022 | (6) Hamilton-Wenham Generals at (2) Amesbury Redhawks | Graf Rink |
| February 19, 2022 | (2) Rockport Vikings at (3) Hamilton-Wenham Generals | PINGREE SCHOOL |
| February 21, 2022 | (3) Hamilton-Wenham Generals at (1) Amesbury Redhawks
Newburyport Bank Classic |
Graf Rink |
| February 23, 2022 | (4) Hamilton-Wenham Generals at (4) Haverhill Hillies
H-W wins in OT |
Graf Rink |
| March 05, 2022 | (1) Hamilton-Wenham Generals at (4) Cohasset/Hull Skippers
Boys Division 4 Tournament |
Connell Memorial Rink |
