| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (10) Wareham/Carver Vikings at (4) Upper Cape Tech Rams | Gallo Arena |
| December 18, 2019 | (7) Dennis-Yarmouth Dolphins at (3) Wareham/Carver Vikings | Gallo Arena |
| December 21, 2019 | (4) Wareham/Carver Vikings at (5) Dighton-Rehoboth/Seekonk Falcons | New England Sports Village |
| December 28, 2019 | (0) Nauset Warriors at (3) Wareham/Carver Vikings | Gallo Arena |
| January 01, 2020 | (3) Apponequet/Old Colony Lakers at (6) Wareham/Carver Vikings | Gallo Arena |
| January 04, 2020 | (3) Wareham/Carver Vikings at (3) Greater New Bedford Vo-Tech Bears | Hetland Arena |
| January 11, 2020 | (6) Somerset Berkley Raiders at (3) Wareham/Carver Vikings | Gallo Arena |
| January 12, 2020 | (4) Wareham/Carver Vikings at (3) Old Rochester/Fairhaven Bulldogs | Tabor Academy |
| January 15, 2020 | (1) Bourne Canalmen at (3) Wareham/Carver Vikings | Gallo Arena |
| January 18, 2020 | (5) Dighton-Rehoboth/Seekonk Falcons at (1) Wareham/Carver Vikings | Gallo Arena |
| January 20, 2020 | (7) Wareham/Carver Vikings at (2) Mashpee/Monomoy Monarchs | Hyannis Youth and Community Center |
| January 25, 2020 | (3) Wareham/Carver Vikings at (4) Apponequet/Old Colony Lakers | Driscoll Arena |
| January 29, 2020 | (4) Greater New Bedford Vo-Tech Bears at (5) Wareham/Carver Vikings | Gallo Arena |
| February 01, 2020 | (3) Wareham/Carver Vikings at (1) Nauset Warriors | Charles Moore Arena |
| February 05, 2020 | (1) Old Rochester/Fairhaven Bulldogs at (3) Wareham/Carver Vikings | Gallo Arena |
| February 08, 2020 | (6) Wareham/Carver Vikings at (7) Somerset Berkley Raiders | Driscoll Arena |
| February 10, 2020 | (4) Wareham/Carver Vikings at (1) Dennis-Yarmouth Dolphins | Tony Kent Arena |
| February 12, 2020 | (2) Wareham/Carver Vikings at (3) Bourne Canalmen | Gallo Arena |
| February 17, 2020 | (4) Mashpee/Monomoy Monarchs at (3) Wareham/Carver Vikings | Gallo Arena |
| February 19, 2020 | (3) Upper Cape Tech Rams at (6) Wareham/Carver Vikings | Gallo Arena |
| February 25, 2020 | (2) Wareham/Carver Vikings at (8) Whitman-Hanson Panthers
Boys D2 S Playoff |
Gallo Arena |
