I have seen that randomly happen with other games from time to time, usually if I have pressed cancel or re-started it has never come back. If your shutting down Windows 8 that's basically like hibernating Windows 7. Windows 8 only actually has a proper re start once a month for Windows Update, unless you re start manually, so that could be something to try.
As it only happens in a Windowed mode i'm really not too sure. Have you tried the usual of having the latest
Direct X runtime updates installed and graphics drivers. I find on Windows 8 for some older games to work i need to have tried updating Direct x.
Although not ideal you can probably hide that error, along with most other errors by making the following change in the registry editor:
HKEY_LOCAL_MACHINE > SYSTEM > CurrentControlSet > Control > Windows
Modify the "ErrorMode" key value from 0 to 2 and re start your computer.
0: shows all error messages
1: hides windows error messages
2: two hides application error messages
That is really not ideal though as you could miss important error messages, such as a game missing a DLL file to function or something like that, so I probably wouldn't do that.