 After three consecutive 20-goal seasons, his offensive production declined in the 1931–32 season.Bailey still helped Toronto win the Stanley Cup in 1932, scoring the Cup-winning goal in game 3 of the finals.Bailey's career came to an abrupt end on December 12, 1933, when he was hit from behind by Eddie Shore of the Boston Bruins, and hit his head on the ice, fracturing his skull; he convulsed on the ice of the Boston Garden.