| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (3) Barnstable Red Hawks at (0) Old Rochester Bulldogs | Gallo Arena |
| December 16, 2019 | (0) Martha's Vineyard Vineyarders at (5) Old Rochester Bulldogs | Tabor Academy |
| December 19, 2019 | (1) Marshfield Rams at (6) Old Rochester Bulldogs | Tabor Academy |
| December 27, 2019 | (3) Sandwich Lady Knights at (2) Old Rochester Bulldogs
Judy Gormley Tournament |
Gallo Arena |
| December 28, 2019 | (1) Marshfield Rams at (5) Old Rochester Bulldogs
Gormley Tournament |
Gallo Arena |
| December 30, 2019 | (1) Hanover Hawks at (1) Old Rochester Bulldogs | Tabor Academy |
| January 02, 2020 | (1) Plymouth Blue Eagles at (1) Old Rochester Bulldogs | Tabor Academy |
| January 06, 2020 | (5) Bishop Stang Spartans at (1) Old Rochester Bulldogs | Tabor Academy |
| January 11, 2020 | (5) Old Rochester Bulldogs at (1) Marshfield Rams | Hobomock Arena |
| January 18, 2020 | (2) Old Rochester Bulldogs at (3) Ursuline Academy Bears
Vineyard Tournament |
Martha's Vineyard Arena |
| January 19, 2020 | (5) Old Rochester Bulldogs at (2) Scituate Sailors
Nan Rheault Tournament - Martha's Vineyard |
Martha's Vineyard Arena |
| January 22, 2020 | (0) Old Rochester Bulldogs at (3) Nauset/Monomoy Warriors | Charles Moore Arena |
| January 25, 2020 | (3) Old Rochester Bulldogs at (4) Norwell | The Bog |
| January 29, 2020 | (2) Old Rochester Bulldogs at (4) Bishop Stang Spartans | Hetland Arena |
| February 01, 2020 | (0) Old Rochester Bulldogs at (1) Sandwich Lady Knights | Gallo Arena |
| February 05, 2020 | (0) Old Rochester Bulldogs at (5) Hanover Hawks | Zapustas Arena |
| February 08, 2020 | (7) Norwell at (1) Old Rochester Bulldogs | Travis Roy Arena |
| February 13, 2020 | (1) Old Rochester Bulldogs at (2) Barnstable Red Hawks | Hyannis Youth and Community Center |
| February 17, 2020 | (1) Nauset/Monomoy Warriors at (0) Old Rochester Bulldogs | Tabor Academy |
| February 19, 2020 | (2) Old Rochester Bulldogs at (3) Plymouth Blue Eagles | Armstrong Arena |
