| Date & Time | Game | Venue |
|---|---|---|
| December 18, 2019 | (4) Duxbury Dragons at (0) Quincy Presidents | Quincy Youth Arena |
| December 21, 2019 | (0) Whitman-Hanson Panthers at (3) Duxbury Dragons | The Bog |
| December 23, 2019 | (2) Xaverian Hawks at (0) Duxbury Dragons | The Bog |
| December 27, 2019 | (2) Bridgewater-Raynham Trojans at (6) Duxbury Dragons
Oyster Cup Holiday Tournament |
The Bog |
| December 28, 2019 | (3) Natick Red Hawks at (3) Duxbury Dragons
Island Creek Oysters Cup Championship Game |
The Bog |
| December 30, 2019 | (3) Duxbury Dragons at (3) Canton Bulldogs | Canton Ice House |
| January 04, 2020 | (1) Silver Lake Lakers at (5) Duxbury Dragons | The Bog |
| January 08, 2020 | (1) Duxbury Dragons at (4) Plymouth North Eagles | Armstrong Arena |
| January 18, 2020 | (0) Pembroke Titans at (8) Duxbury Dragons | The Bog |
| January 20, 2020 | (0) Duxbury Dragons at (0) Marshfield Rams
Green Cup - Duxbury wins 1-0 in SO |
Hobomock Arena |
| January 22, 2020 | (3) Duxbury Dragons at (0) Silver Lake Lakers | Hobomock Arena |
| January 25, 2020 | (0) Quincy Presidents at (6) Duxbury Dragons | The Bog |
| January 27, 2020 | (4) Hingham Harbormen at (0) Duxbury Dragons | The Bog |
| January 29, 2020 | (4) Duxbury Dragons at (2) Plymouth South Panthers | Armstrong Arena |
| February 01, 2020 | (0) Plymouth North Eagles at (1) Duxbury Dragons | The Bog |
| February 03, 2020 | (3) North Quincy Red Raiders at (1) Duxbury Dragons | The Bog |
| February 05, 2020 | (5) Duxbury Dragons at (2) Whitman-Hanson Panthers | Rockland Arena |
| February 08, 2020 | (1) Scituate Sailors at (3) Duxbury Dragons | The Bog |
| February 12, 2020 | (1) Duxbury Dragons at (2) Hanover Hawks | Hobomock Arena |
| February 15, 2020 | (6) Arlington Catholic Cougars at (2) Duxbury Dragons
Buddy Ferreira Classic |
Falmouth Ice Arena |
| February 17, 2020 | (2) Archbishop Williams Bishops at (2) Duxbury Dragons
Duxbury Win in SO - Buddy Ferreira Classic |
Falmouth Ice Arena |
| February 19, 2020 | (3) Duxbury Dragons at (0) Austin Prep Cougars
Buddy Ferreira Classic |
Falmouth Ice Arena |
| February 27, 2020 | (2) Mansfield Hornets at (3) Duxbury Dragons
Boys D1S Playoff |
Gallo Arena |
| February 29, 2020 | (3) Walpole Timberwolves at (2) Duxbury Dragons
Boys D1S Playoff |
Gallo Arena |
