CM 97/98
In case you didn't know the current best managing game is Football Manager which used to be known as Championship Manager.
Taken from Wikipedia...
The Eidos / Sports Interactive split
The creators of Championship Manager, SI Games, split with publishers Eidos, and signed a deal with Sega, to continue the series under the new name, Football Manager. After the split, both parties kept their intellectual property. SI Games kept the base code, the game database and programming of the game, whilst Eidos kept the name "Championship Manager" and its interface.
The reasons for the split have never been revealed, although it is generally felt that Sports Interactive enjoy far greater creative freedom under Sega.
The former working partners are now in direct competition - Eidos and Beautiful Game Studios producing future Championship Manager titles, and Sega and Sports Interactive with Football Manager.
Although under a different name, Football Manager is very similar in gameplay terms to the previous CM games and preferred by original CM gamers, whereas CM5 is a totally new game due to it being written almost from scratch by a new development team.
This emergence of the Football Manager series and the fierce marketing battle between the two could spell danger for EA Sports' Total Club Manager series and other, less successful football management games.
The newer ones are still superb and obviously have a lot more to them, but the older champ series were the best.