Game crashes in career mode when advancing time past a specific date

I am in the third season of this save and when I advance past a specific day (3 days before the next match) the game crashes. There was a bug like this about 4 months ago which apparently was fixed back then, but it somehow got reintroduced again. 

Bought the game through Steam and playing it on PC. 

Thing I tried: 
- Verifiying Integrity of game files
- Loading an older save (Still crashes at the same date)
- Deleting all my settings 
- Restarting the PC 
- Updating my graphics drivers
- Starting the game in admin mode 

This essentially bricks my save file. Please fix this bug