I have always been a huge fan of this game, played it for hours and hours when I was younger, a couple of mate and I would regularly pull an all nighter fueled by coffee and fags playing this. Anyway, the 01/02 season was my favourite and some other very clever fans over on Championship Manager 2001/2002 Website have updated the data to this years teams, leagues and players but still the old game. I started playing earlier this year with the 12/13 data but after a few weeks ran out of time and then lost interest. Started again this weekend, somehow managed to find 10'odd hours and won Serie A with Juve.
Anyway, I would highly recommend downloading the game (free from Eidos Interactive) and the patches, all available from the link above.
I played one of the first versions of cm in my youth (cm2 i think). I played it to death. Would get food and hurry back to the PC and then play it until my head started nodding, very sad I know. Went through so many seasons until eventually players wouldn't sign contracts because beyond 2 or 3 years didn't exist in the game. Also had so much money that the game crashed when i got past a certain amount. Had to restore my saved games to spend the money but couldn't because of the first reason i gave. There was also a bug in the game (later fixed), which meant when another team approached me to become their manager it would automatically accept for me. That was really annoying. A good game though. I dont have enough time to scratch my a*se these days.
I have lost countless hours to this game, specifically the 2001-2002 version.
Its amazing that such an old game still goes very strongly. A legend of it's own making.
I loved CM2...as Arsenal I was undefeated for 4 seasons until Chelmsford (of all teams) beat me 1-0