I'm one of probably 5 Americans who have this game. My dad bought it when he visited England. It seemed odd to me that the CD case's end label is upside down compared to all my US market games. I wonder if that's the standard orientation over there.
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I don't have much help to offer unfortunately.
I tried installing this game on a Win2k machine, as well as XP, but didn't have any luck. It installs but it won't actually run the game. When trying to run the game the CD starts to spin up, but then it dies back down and there's no game process running. Same behavior under both OS. I noticed this thread where somebody else was having the same problem:
FA Premier League Manager 99
I tried using the compatibility options in XP, but it didn't make any difference. There's some way to unlock those options in win2k, but apparently it's not going to do any good regardless.
Back when I played this game it was under Win95 with an S3 Virge 4MB. Processor was a Cyrix 6x86 133MHz (P166+ model) which seemed a bit slow. There's a hardware acceleration option in the game which didn't really work right with that video card (nothing ever did). It ran but it didn't render textures, I suppose it didn't have enough texture memory. Software rendering mode worked fine though.
I had a Geforce2 MX under Win98SE at one point, but I don't remember if I ever ran this game on that combination.