Bay State Conference - Carey Division
| Date & Time | Division | Game | Venue |
|---|---|---|---|
| February 21, 2019 | Boys | (4) Wellesley Raiders at (1) Waltham Hawks | Veterans Memorial Rink |
| February 21, 2019 | Boys | (5) Framingham Flyers at (2) Medford Mustangs
CAHOON CUP CHAMPIONSHIP |
Burlington Ice Palace |
| February 20, 2019 | Boys | (2) Dennis-Yarmouth Dolphins at (3) Brookline Warriors | Walter Brown Arena |
| February 19, 2019 | Boys | (3) Framingham Flyers at (1) Burlington Red Devils
CAHOON CUP |
Burlington Ice Palace |
| February 19, 2019 | Boys | (0) Newton North Tigers at (3) Waltham Hawks | Bentley Arena |
| February 19, 2019 | Boys | (2) Natick Red Hawks at (2) Brockton Boxers | Asiaf Skating Arena |
| February 19, 2019 | Boys | (1) Wellesley Raiders at (0) Walpole Timberwolves | Rodman Arena |
| February 16, 2019 | Boys | (3) Canton Bulldogs at (0) Natick Red Hawks | Chase Arena |
| February 16, 2019 | Boys | (4) Xaverian Hawks at (6) Framingham Flyers | Loring Arena |
| February 16, 2019 | Boys | (2) Newton South Lions at (2) Newton North Tigers | John A. Ryan Arena |
| February 16, 2019 | Boys | (2) Taunton Tigers at (6) Brookline Warriors | Walter Brown Arena |
