Chicago Cubs. Have not won since 1908
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The New York Yankees won the World Series for 5 years in a row in 1949, 19450, 1951, 1952, and 1953. There was no there such win streak in MLB history. The closest was another NY Yankee 4 streak World Series wins beginning in 1927.
The New York Yankees won 5 consecutive World Series from 1949 -1953.
Their longest streak of not winning the World Series is 24 years, from 1982 to 2006.
Yankees losing streakIn 1913, the Yankees had a streak of thirteen losses and one tie. > two losses to the Browns > a tie and a loss against the Red Sox > four losses to the Athletics > two losses to the Red Sox > four losses to the Indians. The Yankees snapped their skid with a win over the White Sox.
Randy Johnson in the 2001 World Series