NSS 2.13, playing a Brazilian forward in AC Milan, 2008-9 season.
When the Italian League ended, I still had to play the Italian Cup final, the Champions' League semifinal (2nd leg) and final, and a WC qualifier for Brazil.
After the final game of the Italian League, I pressed "play", as usual, to advance time. The days passed immediately, with no incidents and, more importantly, no energy recovery. I was thrown to the Italian Cup game immediately. The same thing happened with the other games - it was as if I played 5 games in one day... only after a new season started did the game go back to normal.
Unfortunately, since the game autosaves at the beginning of a new season, I've lost the save file from the buggy period.