The Cubs won four pennants and two World Series titles over a five-year span. Although they fell to the "Hitless Wonders" White Sox in the 1906 World Series, the Cubs recorded a record 116 victories and the best winning percentage (.763) in Major League history. With mostly the same roster, Chicago won back-to-back World Series championships in 1907 and 1908. Their appearance in three consecutive World Series made the Cubs the first Major League club to play three times in the Fall Classic. Likewise, their back-to-back World Series victories in 1907 and 1908 made them the first club to win two World Series. However, the Cubs have not won a World Series since 1908; this remains the longest championship drought in North American professional sports.
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The Cubs won four pennants and two World Series titles over a five-year span. Although they fell to the "Hitless Wonders" White Sox in the 1906 World Series, the Cubs recorded a record 116 victories and the best winning percentage (.763) in Major League history. With mostly the same roster, Chicago won back-to-back World Series championships in 1907 and 1908. Their appearance in three consecutive World Series made the Cubs the first Major League club to play three times in the Fall Classic. Likewise, their back-to-back World Series victories in 1907 and 1908 made them the first club to win two World Series. However, the Cubs have not won a World Series since 1908; this remains the longest championship drought in North American professional sports.