Collingwood
Collingwood have lost more finals than any other afl team when they loose is referred to as the colliwobbles That's one way to look at it, the other way is that they are the only team good enough to play in so many finals, also please don't leave out they have won the most finals! But they have not won the most Grand finals; that honour belongs to both Carlton and Essendon.
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Essendon, Carlton, Collingwood, Melbourne, ??
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Carlton has won 16 Grand Finals. Although Essendon has also won 16 premierships, it has won only 14 grand finals in this achievement. The premierships of 1897 and 1924 were decided by a round robin finals series and no grand final was played in those years.
As of the year 2010, Essendon and Carlton have each won 16 Premierships. Collingwood has won 15 grand finals, and Melbourne, I believe, might be 4th with 13 Grand Final victories.
Carlton has won 16 Grand Finals, and therefore, 16 Premierships in AFL football.
Collingwood Football Club