During the 1950's and 1960's, Norm Smith coached the Melbourne Football Club to 6 Premierships over 11 seasons, with 11 consecutive finals appearances! Those were the days when only 4 teams made the finals.
None other has even approached that kind of record.
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Jock McHale - Collingwood - 8 Premierships. 1917 (playing coach) 1919, 1927, 1928, 1929, 1930, 1935, 1936 over 40 years at the helm of Collingwood Football Club (also a record for tenure as a league coach)
Norm Smith - Melbourne - 6 Premierships: 1955, 1956, 1957, 1959, 1960, 1964 over only 11 full seasons at the coaching helm of Melbourne Football Club.