| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (3) Middleboro Sachems at (0) Dighton-Rehoboth/Seekonk Falcons | New England Sports Village |
| December 18, 2019 | (9) Brookline Warriors at (1) Middleboro Sachems | Bridgewater Ice Arena |
| December 21, 2019 | (3) Middleboro Sachems at (7) Cohasset/Hull Skippers | Connell Memorial Rink |
| December 23, 2019 | (2) Middleboro Sachems at (4) Sandwich Blue Knights | Gallo Arena |
| December 26, 2019 | (2) Taunton Tigers at (1) Middleboro Sachems | Bridgewater Ice Arena |
| December 28, 2019 | (1) Sandwich Blue Knights at (4) Middleboro Sachems | Bridgewater Ice Arena |
| January 01, 2020 | (2) Sacred Heart Saints at (5) Middleboro Sachems | Bridgewater Ice Arena |
| January 08, 2020 | (2) Cohasset/Hull Skippers at (2) Middleboro Sachems | Bridgewater Ice Arena |
| January 11, 2020 | (9) Norwell Clippers at (0) Middleboro Sachems | Bridgewater Ice Arena |
| January 15, 2020 | (2) Middleboro Sachems at (3) Rockland Bulldogs | Rockland Arena |
| January 18, 2020 | (2) Abington Green Wave at (3) Middleboro Sachems | Bridgewater Ice Arena |
| January 20, 2020 | (4) Middleboro Sachems at (9) Brookline Warriors | Walter Brown Arena |
| January 22, 2020 | (4) East/West Bridgewater Vikings at (2) Middleboro Sachems | Bridgewater Ice Arena |
| January 25, 2020 | (6) Middleboro Sachems at (1) East/West Bridgewater Vikings | Bridgewater Ice Arena |
| February 05, 2020 | (4) Middleboro Sachems at (4) Abington Green Wave | Rockland Arena |
| February 09, 2020 | (5) Rockland Bulldogs at (2) Middleboro Sachems
pp from 02/08 |
Bridgewater Ice Arena |
| February 11, 2020 | (3) Middleboro Sachems at (8) Norwell Clippers | The Bog |
| February 12, 2020 | (1) Middleboro Sachems at (5) Taunton Tigers | Aleixo Arena |
| February 16, 2020 | (2) Dighton-Rehoboth/Seekonk Falcons at (1) Middleboro Sachems | Bridgewater Ice Arena |
| February 17, 2020 | (6) Middleboro Sachems at (4) Sacred Heart Saints | The Bog |
