Montreal Canadiens

Won 1993, 1986, 1979, 1978, 1977, 1976, 1973, 1971, 1969, 1968, 1966, 1965, 1960, 1959, 1958, 1957, 1956, 1953, 1946, 1944, 1931, 1930, 1924, 1916

Runner-up 2021, 1989, 1967, 1955, 1954, 1952, 1951, 1947, 1925, 1917, 1914