OK, I went to sim to this date, and the first thing I noticed was that my May 8th game is away @CLE... is your schedule actually showing CHW for the 8th? Just wanted to check, to make sure we are seeing the same schedule. However, the schedule that I see on the game mirrors the real life schedule to the day and times.
Anyway, I simmed up to 5/7 (gotta love how they went on a 7-game streak without me, LOL) and saved my franchise. I then played the 5/8 game @CLE with no problem. I happened to hit a homerun w/ Ordonez in the 1st, so I decided to play the whole game to see if the flashbacks/replays/highlights were still functioning, and they were. So I'm not sure why yours is crashing and mine isn't... unless you do in fact, have a different schedule.