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The vast majority of times that would require you to restart a league is if there are changes to rosters and you are playing the quickstart baseline MLB league.
There are folks who have been running the same league across multiple versions of OOTP and haven't had to restart.
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World Series championships: 1926, 1931, 1934, 1942, 1944, 1946, 1964, 1967, 1982, 2006, 2011
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