| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2019 | (2) Quincy Presidents at (5) Brookline Warriors | Walter Brown Arena |
| December 14, 2019 | (2) Braintree Wamps at (0) Brookline Warriors | Walter Brown Arena |
| December 18, 2019 | (9) Brookline Warriors at (1) Middleboro Sachems | Bridgewater Ice Arena |
| December 21, 2019 | (4) Brookline Warriors at (1) Newton North Tigers | John A. Ryan Arena |
| December 27, 2019 | (2) Brookline Warriors at (1) Middlebury (Vt.) | Memorial Sport Center |
| December 28, 2019 | (2) Brookline Warriors at (6) Stowe (Vt.)
TOURNAMENT |
Memorial Sport Center |
| January 01, 2020 | (3) Brookline Warriors at (0) Nauset Warriors | Charles Moore Arena |
| January 04, 2020 | (1) Brookline Warriors at (2) Weymouth Wildcats | Connell Memorial Rink |
| January 11, 2020 | (2) Swampscott Big Blue at (3) Brookline Warriors | Walter Brown Arena |
| January 15, 2020 | (4) Walpole Timberwolves at (3) Brookline Warriors | Walter Brown Arena |
| January 18, 2020 | (5) Framingham Flyers at (1) Brookline Warriors | Walter Brown Arena |
| January 20, 2020 | (4) Middleboro Sachems at (9) Brookline Warriors | Walter Brown Arena |
| January 22, 2020 | (2) Brookline Warriors at (3) Natick Red Hawks | Chase Arena |
| January 25, 2020 | (1) Brookline Warriors at (0) Needham Rockets | Babson Skating Center |
| January 29, 2020 | (2) Newton North Tigers at (2) Brookline Warriors | Walter Brown Arena |
| February 01, 2020 | (1) Wellesley Raiders at (2) Brookline Warriors | Walter Brown Arena |
| February 05, 2020 | (5) Milton Wildcats at (4) Brookline Warriors | Walter Brown Arena |
| February 08, 2020 | (1) Nauset Warriors at (4) Brookline Warriors | Walter Brown Arena |
| February 15, 2020 | (5) Brookline Warriors at (2) Cohasset/Hull Skippers | Connell Memorial Rink |
| February 19, 2020 | (2) Plymouth South Panthers at (7) Brookline Warriors | Walter Brown Arena |
| February 20, 2020 | (3) Brookline Warriors at (1) Quincy Presidents | Quincy Youth Arena |
| February 26, 2020 | (7) Brookline Warriors at (3) Dedham Marauders
Boys D2 S Playoff |
Canton Ice House |
| February 29, 2020 | (1) Brookline Warriors at (5) Bishop Feehan Shamrocks
Boys D2 S Playoff |
Canton Ice House |
