1938-39 Eastern Canada Memorial Cup Playoffs

Quarter Final
Best of 3

Perth Blue Wings beat Charlottetown Royals 2 wins to 1.

Semi Finals
Best of 3

Oshawa Generals beat North Bay Trappers 2 wins to none.

Verdun Maple Leafs beat Perth Blue Wings 2 wins to none.

Final
Best of 3

Oshawa Generals beat Verdun Maple Leafs 2 wins to 1.

Oshawa Generals advanced to the 1938-39 Memorial Cup Final.