| Date & Time | Game | Venue |
|---|---|---|
| December 08, 2018 | (1) King Philip Warriors at (1) Ursuline Academy Bears | Jim Roche Community Arena |
| December 10, 2018 | (5) Dedham Marauders at (1) Ursuline Academy Bears | Jim Roche Community Arena |
| December 15, 2018 | (8) Ursuline Academy Bears at (2) St. Joseph Prep/Mount Alvernia The Phoenix | Warrior Ice Arena |
| December 20, 2018 | (5) Ursuline Academy Bears at (3) Oakmont Spartans | Cadillac Ice Arena |
| December 22, 2018 | (3) Ursuline Academy Bears at (4) Peabody/Lynnfield/North Reading Tanners | McVann-O'Keefe Skating Rink |
| December 26, 2018 | (2) Latin Academy/Fontbonne Dragons at (7) Ursuline Academy Bears | Jim Roche Community Arena |
| December 28, 2018 | (6) Wilmington Wildcats at (1) Ursuline Academy Bears | Conte Forum |
| January 05, 2019 | (0) Ursuline Academy Bears at (3) King Philip Warriors | Foxboro Sports Center |
| January 07, 2019 | (2) Ursuline Academy Bears at (3) Brookline Warriors | Walter Brown Arena |
| January 10, 2019 | (3) Ursuline Academy Bears at (2) Latin Academy/Fontbonne Dragons | Shea Memorial Rink |
| January 16, 2019 | (4) Ursuline Academy Bears at (0) Oakmont Spartans | Jim Roche Community Arena |
| January 21, 2019 | (0) Ursuline Academy Bears at (3) Newton North/South Tigers | John A. Ryan Arena |
| January 24, 2019 | (3) Norwood Mustangs at (5) Ursuline Academy Bears | Jim Roche Community Arena |
| January 27, 2019 | (3) Ursuline Academy Bears at (3) Bishop Fenwick Crusaders | McVann-O'Keefe Skating Rink |
| January 30, 2019 | (9) Ursuline Academy Bears at (9) Quincy/North Quincy Red Raiders | Quincy Youth Arena |
| February 04, 2019 | (4) Newton North/South Tigers at (2) Ursuline Academy Bears | Jim Roche Community Arena |
| February 05, 2019 | (3) Arlington Catholic Cougars at (4) Ursuline Academy Bears | Jim Roche Community Arena |
| February 09, 2019 | (1) Quincy/North Quincy Red Raiders at (7) Ursuline Academy Bears | Jim Roche Community Arena |
| February 13, 2019 | (2) Ursuline Academy Bears at (4) Dedham Marauders | Noble & Greenough School |
| February 27, 2019 | (1) Ursuline Academy Bears at (7) Algonquin/Hudson Titans | New England Sports Center |
