I had the exact same issue. It turned out that my schedule was set up to start on January 1st.
Sporr helped me on this:
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Originally Posted by Sporr
Well, this happened with us when I made some modifications to our schedule one year before all of the off-season stuff had taken place. In order to get it so that we could proceed, I had to change the Starting Date in the schedule screen to January 1st or something like that. Well that worked just fine until the next season. Then the game tried to generate a schedule with the first games played on January 1st, but the Proceed to Next Season process takes you past that point, causing the game to crash. I had to go in and change the Starting Date on the Edit Schedule screen back to April 1 (or whatever you wish). Then, the Proceed worked just fine.
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My game would always crash when generating rookies. And it too would be an .exe type error. So check your schedule and see when it says the season starts. If it is in January or February, change it to the REAL day your season starts (last week of March, first week of April).
Hope it works!