The last time a World Series started in September was the 1955 World Series between the New York Yankees and Brooklyn Dodgers. Game 1 was played September 28.
Only once in MLB history has the entire World Series been played in September. That was in 1918 (Boston Red Sox v. Chicago Cubs) when MLB cut it's regular season short to accommodate the government and it's 'Work or Fight' edict which stated that any male of draft age must either enlist in the service or take a job that directly contributed to the war (World War I) effort. Game 1 of the World Series was played on September 5 and the final game, Game 6, was played on September 11.
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The Cleveland Indians prior to their World Series appearance in 2016 against the Chicago Cubs in which they had lost against the Cubs in seven games the last time they had played in the World Series was in 1997 in which they had played the Florida Marlins and lost to them in seven games. They had also lost in the 1995 World Series to the Atlanta Braves.
The Cubs last won the World Series in 1908. Since then, the Yankees have won 26 World Series.
The last time the cubs were in the world series was 1945. the last time they won was 1907-1908
The Milwaukee Braves defeated the Yankees in seven games in the 1957 World Series. The final game was played in Yankee Stadium.
September 30,1990