| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (0) Weymouth Wildcats at (7) Wellesley Raiders | Wellesley Sports Center |
| December 18, 2019 | (0) Wellesley Raiders at (1) Austin Prep Cougars | Matthews Arena |
| December 21, 2019 | (8) Wellesley Raiders at (1) Framingham Flyers | Loring Arena |
| December 23, 2019 | (1) Needham Rockets at (3) Wellesley Raiders | Travis Roy Ice Arena |
| January 02, 2020 | (7) Wellesley Raiders at (1) Walpole Timberwolves | Rodman Arena |
| January 08, 2020 | (6) Wellesley Raiders at (1) Brookline Warriors | Walter Brown Arena |
| January 15, 2020 | (0) Needham Rockets at (2) Wellesley Raiders | Wellesley Sports Center |
| January 18, 2020 | (5) Wellesley Raiders at (0) Natick Red Hawks | Chase Arena |
| January 20, 2020 | (2) Wellesley Raiders at (1) Matignon Warriors | Stoneham Arena |
| January 22, 2020 | (1) Austin Prep Cougars at (3) Wellesley Raiders | Wellesley Sports Center |
| January 25, 2020 | (0) Milton Wildcats at (3) Wellesley Raiders | Wellesley Sports Center |
| January 29, 2020 | (0) Framingham Flyers at (7) Wellesley Raiders | Wellesley Sports Center |
| February 01, 2020 | (0) Brookline Warriors at (7) Wellesley Raiders | Wellesley Sports Center |
| February 05, 2020 | (4) Wellesley Raiders at (2) Braintree Wamps | Zapustas Arena |
| February 08, 2020 | (7) Wellesley Raiders at (0) Newton North/South Tigers | John A. Ryan Arena |
| February 12, 2020 | (0) Natick Red Hawks at (4) Wellesley Raiders | Wellesley Sports Center |
| February 17, 2020 | (5) Wellesley Raiders at (1) Masconomet Chieftains
NEWBuryport Bank Ice Hockey Classic |
Graf Rink |
| February 19, 2020 | (1) Wellesley Raiders at (0) Shrewsbury Colonials
NEWburyport BANK Tournament |
Graf Rink |
| February 20, 2020 | (1) Woburn Tanners at (2) Wellesley Raiders | Wellesley Sports Center |
| February 29, 2020 | (0) Medfield Warriors at (3) Wellesley Raiders
Girls D2 Playoff |
Canton Ice House |
| March 04, 2020 | (1) Westwood Wolverines at (6) Wellesley Raiders
Girls D2 Quarter Finals |
Warrior Ice Arena |
| March 08, 2020 | (0) Falmouth Clippers at (6) Wellesley Raiders
Girls D2 Semi Finals - Game 29 |
Warrior Ice Arena |
| March 15, 2020 | Canton Bulldogs at Wellesley Raiders
Girls D2 Championship |
TD Garden |
