That I haven't seen before, so I'm not sure of a fix.
When you save a new game, can you play THAT save? I know you can't run the old windows saves, but are you able to play a game you saved on your (MAC?) through crossover?
Second, just out of curiosity:
These are useful registry keys
http://wiki.winehq.org/UsefulRegistryKeys
On the crossover games menu, go to [programs] and [run command]
Select the bottle you're going to use, and type [regedit] (without brackets) into the command you want to run.
In the list that opens in the Crossover bottle registry, go to [software], [wine], [direct3d]
In the direct 3d folder, right click and create a new string (if there isn't one already) called UseGLSL. Right click it and select [modify] and for [value] write [disabled]. If that doesn't work, try [enabled], and if that doesn't work, delete that entry from the bottle registry.
You could also try [software], [wine], [direct3d] and create a string called OffscreenRenderingMode and give it a value [backbuffer] (no brackets). If it doesn't work, set the value to [fbo] (which is the default.
No guarantee it'll work, but I've used these on a couple programs that didn't want to run and as long as you set the registry back again, nothing is lost if it doesn't work.