In the 1928–29 NHL season, Bailey became the league leading goal scorer, scoring 22 goals and 32 points in 44 games. He once again became the Maple Leafs' leading scorer in the 1929–30 season and he was one point short of repeating as leading scorer in the 1930–31 season. His offensive production declined in the 1931–32 season but he was still able to help Toronto win the Stanley Cup in 1932.