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Crashing while in the process of saving is a bad problem. Have you ever made any backups of your league?
In the .lg folder of any of your affected saved games, are any of your .dat files at a size of 0 kb? You can find your .lg folders at: C:\Documents and Settings\(username)\My Documents\Out of the Park Developments\OOTP Baseball 8\data\saved_games
I don't know what you mean when you say that you are playing a regular game. Are you using real players or fake players? Are you playing in a modern year, or are you playing sometime in the past?
Did the game crash while holding your amateur draft or right after one?
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