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As of 2016, no team has won consecutive World Series championships since the New York Yankees in 1998, 1999, and 2000âthe longest such drought in Major League Baseball history.
Team Thatâs Won The Most World Series Titles. The team that has won the most baseball Word Series titles is the New York Yankees and it is not even close. The Bronx Bombers have won World Series title 26 times since they became a professional ball club way back in 1903. Their last World Series title was in 2000.