Jeffrey played for the Maple Leafs in the 1967 Stanley Cup playoffs, though he injured his leg again in the semifinals against the Chicago Black Hawks, before the Maple Leafs defeated the Montreal Canadiens in the 1967 Stanley Cup Finals.
In the 1967 Stanley Cup playoffs, Jeffrey played for the Maple Leafs. However, he sustained another leg injury during the semifinals against the Chicago Black Hawks and still managed to guide the Maple Leafs to victory in the 1967 Stanley Cup Finals over the Montreal Canadiens.