| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (8) Walpole Timberwolves at (0) Newton North Tigers | John A. Ryan Arena |
| December 18, 2019 | (3) Walpole Timberwolves at (1) Needham Rockets | Babson Skating Center |
| December 21, 2019 | (2) Weymouth Wildcats at (2) Walpole Timberwolves | Rodman Arena |
| December 26, 2019 | (2) Longmeadow Lancers at (3) Walpole Timberwolves
Songin Winter Classic |
Rodman Arena |
| December 28, 2019 | (1) Shrewsbury Colonials at (2) Walpole Timberwolves
Sogin winter Classic |
Rodman Arena |
| December 31, 2019 | (6) Norwood Mustangs at (2) Walpole Timberwolves | Rodman Arena |
| January 02, 2020 | (3) Walpole Timberwolves at (3) Wellesley Raiders | Babson Skating Center |
| January 08, 2020 | (7) Braintree Wamps at (1) Walpole Timberwolves | Rodman Arena |
| January 13, 2020 | (0) Walpole Timberwolves at (7) Hingham Harbormen | Pilgrim Arena |
| January 15, 2020 | (4) Walpole Timberwolves at (3) Brookline Warriors | Walter Brown Arena |
| January 18, 2020 | (4) Walpole Timberwolves at (1) Milton Wildcats | Ulin Memorial Rink |
| January 22, 2020 | (3) Needham Rockets at (3) Walpole Timberwolves | Rodman Arena |
| January 25, 2020 | (2) Framingham Flyers at (1) Walpole Timberwolves | Rodman Arena |
| January 29, 2020 | (1) Walpole Timberwolves at (1) Weymouth Wildcats | Connell Memorial Rink |
| February 01, 2020 | (3) Walpole Timberwolves at (3) Braintree Wamps | Zapustas Arena |
| February 03, 2020 | (5) Burlington Red Devils at (0) Walpole Timberwolves | Rodman Arena |
| February 05, 2020 | (2) Natick Red Hawks at (1) Walpole Timberwolves | Rodman Arena |
| February 08, 2020 | (3) Bridgewater-Raynham Trojans at (1) Walpole Timberwolves | Noble & Greenough School |
| February 12, 2020 | (3) Milton Wildcats at (1) Walpole Timberwolves | Rodman Arena |
| February 15, 2020 | (1) King Philip Warriors at (2) Walpole Timberwolves | Rodman Arena |
| February 17, 2020 | (2) Walpole Timberwolves at (1) Marshfield Rams | The Bog |
| February 20, 2020 | (5) Walpole Timberwolves at (2) Concord-Carlisle Patriots | Edge Sports Center |
| February 27, 2020 | (2) Walpole Timberwolves at (1) Braintree Wamps
Boys DIV 1S playoff |
Canton Ice House |
| February 29, 2020 | (3) Walpole Timberwolves at (2) Duxbury Dragons
Boys D1S Playoff |
Gallo Arena |
| March 04, 2020 | (2) Walpole Timberwolves at (1) Falmouth Clippers
Boys D1 S Semifinal |
Gallo Arena |
| March 08, 2020 | (0) Archbishop Williams Bishops at (1) Walpole Timberwolves
Boys D1 South Final |
Gallo Arena |
| March 15, 2020 | Walpole Timberwolves at Belmont Marauders
Boys D1 Championship |
TD Garden |
