It depends on your computer. Go to "preferences", go to "Display and Sound", and untick the bit that says full screen. Click confirm, and you'll find out then whether your computer is compatible with windowed play.
Cheers... just tried it but it said 'Changing the screen settings failed. Make sure your system supports the settings.' Why wouldn't it support them? Any ideas?
Why do you want to play "windowed"? You can press the windows key and go back to your desktop etc if you are wanting to access something else?
RE: Why do you want to play "windowed"? cos I get annoyed with pressing the window key all the time, i'm playing it now, not doing too bad anorl!
Right click on desktop icon, the properties. Then in target have "C:\Program Files\Sports Interactive\Football Manager 2008\fm.exe" --small_screen --windowed