24 games, set by the 1889 Cleveland Spiders.
Since 1900, the team with the longest losing streak in Baseball was the Philadelphia Phillies, who lost 23 consecutive games from July 26 to August 20 in 1961.
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As of the start of the 2007 playoffs, the longest winning streak in a single postseason is 8 games and is held by the 2004 Boston Red Sox and the 2005 Chicago White Sox. The Reds also won Game 7 in '75 and swept all 7 games in the '76 postseason.
The most consecutive World Series lost is 7 by the Chicago Cubs (1945, 1938, 1935, 1932, 1929, 1918, 1910).
The most consecutive games lost in the World Series is 8 by the Philadelphia Phillies (last 4 games in 1915 and all four games in 1950).
The New York Yankees went winless in 9 consecutive games (last 3 games in 1921, all five games in 1922, and the first game in 1923) but one of the games in the 1922 World Series ended in a tie.