The Yankees have won the World Series 27 times, the most out of any team.
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The New York Yankees have won the World Series 27 times, most recently in 2009. They have also appeared in 40 World Series, more than any other team in baseball history.
Most recent- 2009
The Yankees have won the World Series 27 times, the most of any team in baseball. They last won in 2009, when they defeated the Philadelphia Phillies in six games.
Last time they didn’t make it to the playoffs- 2008
In 2008, the Yankees failed to make the playoffs for the first time since 1995, one year after George Steinbrenner had passed away. The team finished the season with a record of 89–73, third place in the AL East behind the eventual World Series champion Tampa Bay Rays and the runner-up Boston Red Sox.