The New York Giants were the first team to lose 6 World Series, losing to the Philadelphia Athletics in 1911, Boston Red Sox in 1912, Philadelphia Athletics in 1913, Chicago White Sox in 1917, New York Yankees in 1923, and Washington Nationals in 1924.
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As of the 2011 season, the New York Yankees have lost the most World Series and won the most World Series. Their WS record is 27-13. Tied for second most World Series losses are the Dodgers and the Giants. The Dodgers WS record is 6-12 and the Giants WS record is 6-12.
Probably the Atlanta Braves.
They lost four straight to the Yankees in 1996, and then were swept by the Yankees in 1999 -- thus eight straight.
The Phillies also lost 8 straight ... the final 4 to the Red Sox in 1915 and all 4 to the Yankees in 1950. Incredibly, the 4 to the Red Sox and the first 3 to the Yankees were all 1 run losses.
Through the 2009 World Series, that is the New York Yankees with 13.
The Dodgers and Giants have lost 12 each.
1907-1909 Detroit Tigers.
The Tigers lost to the Cubs in 1907 and 1908 and to the Pirates in 1909.
This has been "accomplished" twice:
By the 1907, 1908, 1909 Detroit Tigers
1911, 1912, 1913 NY Giants