| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (3) Scituate Sailors at (0) Silver Lake Lakers | Hobomock Arena |
| December 15, 2019 | (2) Norwell Clippers at (2) Scituate Sailors
(Norwell wins 3-2 in a shootout) |
Hobomock Arena |
| December 18, 2019 | (3) Scituate Sailors at (4) Plymouth South Panthers | Armstrong Arena |
| December 21, 2019 | (4) Marshfield Rams at (2) Scituate Sailors | Hobomock Arena |
| December 26, 2019 | (4) Scituate Sailors at (1) Southeastern/Bristol-Plymouth Hawks | Raynham IcePlex |
| December 28, 2019 | (1) Cohasset/Hull Skippers at (5) Scituate Sailors | Hobomock Arena |
| January 02, 2020 | (5) Scituate Sailors at (1) North Quincy Red Raiders | Quincy Youth Arena |
| January 04, 2020 | (0) Coyle & Cassidy Warriors at (5) Scituate Sailors | Hobomock Arena |
| January 08, 2020 | (3) North Quincy Red Raiders at (4) Scituate Sailors | Hobomock Arena |
| January 11, 2020 | (4) Scituate Sailors at (1) Pembroke Titans | Hobomock Arena |
| January 20, 2020 | (2) Concord-Carlisle Patriots at (1) Scituate Sailors | The Bog |
| January 22, 2020 | (1) Scituate Sailors at (2) Plymouth North Eagles | Armstrong Arena |
| January 25, 2020 | (1) Plymouth South Panthers at (9) Scituate Sailors | Hobomock Arena |
| January 29, 2020 | (2) Scituate Sailors at (7) Barnstable Red Hawks | Hyannis Youth and Community Center |
| February 01, 2020 | (1) Pembroke Titans at (8) Scituate Sailors | Hobomock Arena |
| February 02, 2020 | (4) Whitman-Hanson Panthers at (1) Scituate Sailors | Hobomock Arena |
| February 05, 2020 | (0) Scituate Sailors at (2) Hanover Hawks | Hobomock Arena |
| February 08, 2020 | (1) Scituate Sailors at (3) Duxbury Dragons | The Bog |
| February 12, 2020 | (6) Scituate Sailors at (1) Attleboro Blue Bombardiers | New England Sports Village |
| February 15, 2020 | (0) Quincy Presidents at (2) Scituate Sailors | Hobomock Arena |
| February 17, 2020 | (0) Scituate Sailors at (3) Hanover Hawks
Gould Tournament |
Hobomock Arena |
| February 19, 2020 | (7) Scituate Sailors at (0) Pembroke Titans
Gould Tournament |
Hobomock Arena |
| February 26, 2020 | (7) Scituate Sailors at (3) Southeastern/Bristol-Plymouth Hawks
Boys D2 S Playoff |
Gallo Arena |
| February 29, 2020 | (0) Scituate Sailors at (2) Whitman-Hanson Panthers
Boys D2 S Playoff |
Gallo Arena |
