| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2019 | (0) Milton Wildcats at (3) Ursuline Academy Bears | Jim Roche Community Arena |
| December 14, 2019 | (0) Bishop Feehan Shamrocks at (5) Ursuline Academy Bears | Jim Roche Community Arena |
| December 18, 2019 | (1) Arlington Catholic Cougars at (3) Ursuline Academy Bears | Jim Roche Community Arena |
| December 21, 2019 | (5) Ursuline Academy Bears at (0) Leominster Blue Devils | Wallace Civic Center |
| December 28, 2019 | (5) Ursuline Academy Bears at (2) Dover-Sherborn/Hopkinton Raiders | Blackstone Valley Ice Arena |
| January 04, 2020 | (0) Oakmont Spartans at (6) Ursuline Academy Bears | Jim Roche Community Arena |
| January 07, 2020 | (3) Ursuline Academy Bears at (4) Norwood Mustangs | Bajko Memorial Rink |
| January 09, 2020 | (6) Ursuline Academy Bears at (1) Latin Academy/Fontbonne Dragons | Shea Memorial Rink |
| January 12, 2020 | (3) Ursuline Academy Bears at (0) Oakmont Spartans | Veterans Memorial Ice Rink |
| January 14, 2020 | (2) Dover-Sherborn/Hopkinton Raiders at (2) Ursuline Academy Bears | Jim Roche Community Arena |
| January 18, 2020 | (2) Old Rochester Bulldogs at (3) Ursuline Academy Bears
Vineyard Tournament |
Martha's Vineyard Arena |
| January 19, 2020 | (4) Ursuline Academy Bears at (1) Martha's Vineyard Vineyarders
Nan Rheault Tournament |
Martha's Vineyard Arena |
| January 26, 2020 | (6) Ursuline Academy Bears at (2) Dedham Marauders | Noble & Greenough School |
| January 28, 2020 | (4) Latin Academy/Fontbonne Dragons at (4) Ursuline Academy Bears | Jim Roche Community Arena |
| February 01, 2020 | (5) Ursuline Academy Bears at (0) Bishop Feehan Shamrocks | New England Sports Village |
| February 07, 2020 | (2) Dedham Marauders at (1) Ursuline Academy Bears | Jim Roche Community Arena |
| February 08, 2020 | (3) Brookline Warriors at (3) Ursuline Academy Bears | Conte Forum |
| February 12, 2020 | (1) Ursuline Academy Bears at (6) King Philip Warriors | Foxboro Sports Center |
| February 15, 2020 | (0) Leominster Blue Devils at (2) Ursuline Academy Bears | Jim Roche Community Arena |
| February 19, 2020 | (3) King Philip Warriors at (3) Ursuline Academy Bears | Jim Roche Community Arena |
| February 29, 2020 | (3) Winchester Red & Black at (4) Ursuline Academy Bears
Girls D2 Playoff |
Canton Ice House |
| March 04, 2020 | (0) Ursuline Academy Bears at (5) Canton Bulldogs
Girls D2 Quarter Finals |
Warrior Ice Arena |
