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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.
New York Yankee Pitcher Whitey Ford Has the Most World Series Wins of All Time: 10. Andy Pettitte is baseballâs all-time winningest postseason pitcher, tossing for 19 playoff victories all together. But he doesnât have the most World Series wins. That honor belongs to another New York Yankee, Whitey Ford, who won 10 on the grandest postseason stage of all.