Football Manager 2

The gameplay, compared with modern versions of the game, was incredibly primitive with a very small database of players whose form failed to vary anything like as much as it would in the real world. And the transfer market also left a lot to be desired with a fixed price for most players. And , of course, the longer you played the game the more the finances would creep up and up. You could be the worst money manager in the world yet the finances of the club would creep resolutely upwards.

The graphics consisted of matchstick men on a matt black pitch - you had no idea who was who - but whenever Tony Woodcock scored it would always be the crossed from the left wing and in and the far post. And with the poor graphics came the lack of any physical interaction with the game. A real plus would have been some kind of control over those matchstick players. I can't ever remember being sacked either - unless I intentionally sold everyone and tried to start from scratch - not a good idea on a computer game - let alone the real world.
All in all hours of fun though it didn't seem to matter who you managed. If you took on Chelsea or Crewe Alexandra you eventually would become Division 1 champions and FA Cup winners and League Cup winners all in the same season - something that would not happen in the real world. I think modern processors have allowed for this fault on modern simulations - though even today - if you spend long enough on a game you can always reach the top.
There were many imitations to this game at the time - League Challenge being one - but none came close to the real McCoy that was Football Manager and Football Manager 2.