Boys Division 2 North
| Date & Time | Division | Home | Away | Venue |
|---|---|---|---|---|
| Feb. 25 (Time TBA) | Boys | (5) Wilmington Wildcats | (2) Wakefield Warriors | Ristuccia Memorial Arena |
| February 26, 2019 | Boys | (5) Triton Vikings | (1) North Andover Scarlet Knights | Chelmsford Forum |
| February 26, 2019 | Boys | (1) Lincoln-Sudbury Warriors | (0) Lowell Catholic Crusaders | O'Brien Arena |
| February 26, 2019 | Boys | (5) Gloucester Fishermen | (6) Danvers Falcons | Stoneham Arena |
| February 26, 2019 | Boys | (2) Tewksbury Redmen | (1) Lynnfield Pioneers | Chelmsford Forum |
| February 26, 2019 | Boys | (4) Boston Latin Wolfpack | (1) Somerville Highlanders | John A. Ryan Arena |
| February 26, 2019 | Boys | (5) Marblehead Magicians | (2) Pentucket Panthers | Stoneham Arena |
| February 26, 2019 | Boys | (2) Winthrop Vikings | (6) Stoneham Spartans | O'Brien Arena |
| February 27, 2019 | Boys | (5) Masconomet Chieftains | (2) Wilmington Wildcats | O'Brien Arena |
| March 01, 2019 | Boys | (1) Lincoln-Sudbury Warriors | (2) Tewksbury Redmen | Chelmsford Forum |
| March 01, 2019 | Boys | (3) Danvers Falcons | (0) Marblehead Magicians | Stoneham Arena |
| March 01, 2019 | Boys | (3) Boston Latin Wolfpack | (1) Stoneham Spartans | Chelmsford Forum |
| March 01, 2019 | Boys | (1) Masconomet Chieftains | (5) Triton Vikings | Stoneham Arena |
| March 05, 2019 | Boys | (3) Triton Vikings | (8) Boston Latin Wolfpack | Tsongas Center |
| March 05, 2019 | Boys | (4) Tewksbury Redmen | (1) Danvers Falcons | Tsongas Center |
| March 11, 2019 | Boys | (6) Tewksbury Redmen | (4) Boston Latin Wolfpack | Tsongas Center |
Boys Division 2 South
| Date & Time | Division | Home | Away | Venue |
|---|---|---|---|---|
| February 25, 2019 | Boys | (8) Sandwich Blue Knights | (6) Brookline Warriors | Gallo Arena |
| February 25, 2019 | Boys | (0) Dedham Marauders | (1) Medway Mustangs | Noble & Greenough School |
| February 26, 2019 | Boys | (3) Medfield Warriors | (0) Nauset Warriors | Gallo Arena |
| February 26, 2019 | Boys | (0) Quincy Presidents | (2) North Attleboro Red Rocketeers | Canton Ice House |
| February 26, 2019 | Boys | (2) Wareham/Carver Vikings | (4) Bishop Feehan Shamrocks | Gallo Arena |
| February 27, 2019 | Boys | (4) Southeastern/Bristol-Plymouth Hawks | (3) Sandwich Blue Knights | Canton Ice House |
| February 27, 2019 | Boys | (3) Plymouth North Eagles | (4) Oliver Ames Tigers | Gallo Arena |
| February 27, 2019 | Boys | (3) Norwood Mustangs | (2) Scituate Sailors | Canton Ice House |
| February 27, 2019 | Boys | (6) Canton Bulldogs | (0) Medway Mustangs | Canton Ice House |
| March 02, 2019 | Boys | (2) Westwood Wolverines | (1) Bishop Feehan Shamrocks | Canton Ice House |
| March 02, 2019 | Boys | (0) Southeastern/Bristol-Plymouth Hawks | (4) Medfield Warriors | Gallo Arena |
| March 02, 2019 | Boys | (2) North Attleboro Red Rocketeers | (3) Norwood Mustangs | Pirelli Veterans Arena |
| March 02, 2019 | Boys | (3) Canton Bulldogs | (0) Oliver Ames Tigers | Canton Ice House |
| March 05, 2019 | Boys | (2) Medfield Warriors | (3) Westwood Wolverines | Gallo Arena |
| March 05, 2019 | Boys | (6) Canton Bulldogs | (1) Norwood Mustangs | Gallo Arena |
| March 10, 2019 | Boys | (0) Westwood Wolverines | (8) Canton Bulldogs | Gallo Arena |
