In FM 07 I won Serie A with Milan about 4 times in a row (it was pretty easy with them tbh), then moved to England and won the prem with Chelsea, then moved to Spain and won La Liga with Athletico, then moved back to italy and won Serie A with Fiorentina, then moved to germany and won the Bundesliga with Bayern.
That was all on the same save. Sounds impressive but it wasn't to be honest. Started with Milan who were already amazing. Made some key signings but that was it really. Pretty much any tactic worked with them. Then every time I moved the team I went to was already really good and I didn't have to do much to win the leagues.
Don't think i could do that on FM 09, its much harder.