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This was a lot of fun to cobble together!
When the Yankees won the 1937 World Series, they took the lead for good. Boston, the Athletics, and the Yankees were tied with 5.
Then, when they lost to the Braves in 1957, their loss total was 7, more than any other team had WON. Their 1976 loss to Cincinnati was their 11th loss -- more losses than any other team has won to this date.
The Cardinals are the Yankees worst team, beating them 4 times. The Dodgers are next with 3.
Wanna know a fun fact? The very first team with 2 World Series titles was the CUBS. After winning # 2 (consecutive) they haven't won since, though they have made 2 appearances.