| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (3) Pembroke Titans at (5) Whitman-Hanson Panthers | Rockland Arena |
| December 18, 2019 | (3) North Quincy Red Raiders at (1) Pembroke Titans | Hobomock Arena |
| December 21, 2019 | (5) Plymouth South Panthers at (5) Pembroke Titans | Hobomock Arena |
| December 23, 2019 | (0) Pembroke Titans at (7) Bridgewater-Raynham Trojans | Bridgewater Ice Arena |
| December 30, 2019 | (3) Cohasset/Hull Skippers at (1) Pembroke Titans | Hobomock Arena |
| January 04, 2020 | (1) Pembroke Titans at (6) Hanover Hawks | Hobomock Arena |
| January 08, 2020 | (4) Silver Lake Lakers at (2) Pembroke Titans | Hobomock Arena |
| January 11, 2020 | (4) Scituate Sailors at (1) Pembroke Titans | Hobomock Arena |
| January 15, 2020 | (8) Marshfield Rams at (3) Pembroke Titans | Hobomock Arena |
| January 18, 2020 | (0) Pembroke Titans at (8) Duxbury Dragons | The Bog |
| January 20, 2020 | (2) Bridgewater-Raynham Trojans at (1) Pembroke Titans | Hobomock Arena |
| January 22, 2020 | (0) Pembroke Titans at (4) North Quincy Red Raiders | Quincy Youth Arena |
| January 29, 2020 | (1) Pembroke Titans at (2) Quincy Presidents | Quincy Youth Arena |
| January 31, 2020 | (3) Norwell Clippers at (0) Pembroke Titans
Makeup from 12-28 |
Bridgewater Ice Arena |
| February 01, 2020 | (1) Pembroke Titans at (8) Scituate Sailors | Hobomock Arena |
| February 05, 2020 | (0) Pembroke Titans at (6) Plymouth North Eagles | Armstrong Arena |
| February 08, 2020 | (8) Hanover Hawks at (1) Pembroke Titans | Hobomock Arena |
| February 12, 2020 | (3) Pembroke Titans at (5) Plymouth South Panthers | Armstrong Arena |
| February 15, 2020 | (3) Pembroke Titans at (3) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| February 17, 2020 | (7) Norwell Clippers at (0) Pembroke Titans
GOULD TOURNEY |
Hobomock Arena |
| February 19, 2020 | (7) Scituate Sailors at (0) Pembroke Titans
Gould Tournament |
Hobomock Arena |
