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Championship manager 01-02 for me is the best football managing game out there. This simple, classic and absorbing game is made by the people that have now turned into the football manager series.
This game does not have any fancy 3d or even 2d animated pitch graphics. Every match you play is displayed via scrolling text. This is simple but very effective.
Some of you may be put off by this game being many years old. Luckily for you there are fan made updates on the internet that you can download for free which make most of the clubs and players in the world up to date including their in game stats. All of the teams are in the right leagues as well.
The thing that makes this game so great is the way in which it makes you focus on what players you have and how to optimise your tactics and team to play their best. If you like taking over the world of football you could start out as a rich team and buy buy buy.
All in all this simple and enjoyable managerial classic offers all the best aspects of managerial games at an affordable price and it doesn't take months to do a whole season! (coughfootballmanagercough)