Mel Stottlemyre has the most losses in Yankees history with 139.
The Yankees lost the most games as a team in 1908. At that time they were known as the New York Highlanders and they had a record of 51-103.
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The New York Yankees have lost 88 World Series games. Of course, they have been in 39 World Series so it would only make sense that they have lost the most games. They have also won the most World Series games with 130.
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Team = Yankees Player = Arod
The team with the worst win percentage against the Yankees is the Astros (.111). They are 1-8 all time against NY. The team with the most losses against New York is Baltimore. The Orioles have a record of 843-1241 all time against New York.
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