| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2019 | (1) Dedham Marauders at (1) Winthrop Vikings | Larsen Rink |
| December 14, 2019 | (3) Dedham Marauders at (2) Dover-Sherborn/Weston Raiders | Chase Arena |
| December 18, 2019 | (1) Westwood Wolverines at (2) Dedham Marauders | Noble & Greenough School |
| December 21, 2019 | (7) Dedham Marauders at (1) Bellingham Blackhawks | Pirelli Veterans Arena |
| December 26, 2019 | (0) OBryant Tigers at (6) Dedham Marauders
East Boton Deep Freeze |
Lt. Porrazzo Memorial Rink |
| December 27, 2019 | (1) Ashland Clockers at (7) Dedham Marauders
Deep Freeze Cancer Tournament |
Lt. Porrazzo Memorial Rink |
| January 04, 2020 | (4) Dedham Marauders at (1) Medfield Warriors | Pirelli Veterans Arena |
| January 05, 2020 | (2) North Attleboro Red Rocketeers at (7) Dedham Marauders | Noble & Greenough School |
| January 08, 2020 | (1) Norton Lancers at (5) Dedham Marauders | Noble & Greenough School |
| January 11, 2020 | (5) Dedham Marauders at (2) Ashland Clockers | Loring Arena |
| January 18, 2020 | (2) Holliston Panthers at (2) Dedham Marauders | Noble & Greenough School |
| January 22, 2020 | (2) Dedham Marauders at (3) Medway Mustangs | Pirelli Veterans Arena |
| January 25, 2020 | (2) Dover-Sherborn/Weston Raiders at (5) Dedham Marauders | Noble & Greenough School |
| January 29, 2020 | (2) Dedham Marauders at (6) Hopkinton Hillers | New England Sports Center |
| February 01, 2020 | (1) Bellingham Blackhawks at (7) Dedham Marauders | Noble & Greenough School |
| February 05, 2020 | (3) Norwood Mustangs at (1) Dedham Marauders | Noble & Greenough School |
| February 08, 2020 | (9) Dedham Marauders at (3) Norton Lancers | Foxboro Sports Center |
| February 09, 2020 | (1) Whitman-Hanson Panthers at (1) Dedham Marauders | Noble & Greenough School |
| February 12, 2020 | (5) Dedham Marauders at (1) Latin Academy Dragons | Matthews Arena |
| February 15, 2020 | (1) Medway Mustangs at (0) Dedham Marauders | Noble & Greenough School |
| February 26, 2020 | (7) Brookline Warriors at (3) Dedham Marauders
Boys D2 S Playoff |
Canton Ice House |
