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OOTP 14 looks for a matching logo for each team whenever you start the game and a logo is required first time. For example you start OOTP, load a league which game date is 2010/08/20. Then you open a team screen which has the logo in the upper left corner. The game date's year at that moment will be taken to determine which logo is the correct one.
So currently OOTP 14 does not care about season start or season end.
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