From what I understnd the most successful sporting team in history is the All Blacks, New Zealands International Rugby squad. Based on overall win ratio over almost 100 years of 75% and the fact that the All Blacks have held the top ranking in the world for longer than all other countries combined.
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The New York Yankees, because they won 17 American League East Division Championships, 40 American League Championships, and 27 World Series Championships equaling 84 Championships. Also in 1999 they were put as the world's best Baseball team.
The New York Yankees with 26 World Series Championships. Next would be the Montreal Canedians with 24 Stanley Cup victories, the Boston Celtics with 17 NBA titles and the most Superbowls wins are 5 shared by the Dallas Cowboys, San Francisco 49ners and the Pittsburgh Steelers.