Mmmmm, tough one. I'm inclined to go with Mourinho's first title win in first place. 2nd, Conte season one for an unexpected title win plus I really enjoyed the football played that year and the way Conte celebrated prior to the big sulks in season. 2. Third, 1996/97, first time I had seen us win anything so a special season plus that year has my favourite game of all, the 4-2 come back win in the cup against Liverpool, amazing atmosphere, even with the shed end missing!
Honourable mentions, Ancelotti season 1 for the number of goals scored but agree with Argo, could have easily messed up and finished 2nd. 2012, once RDM took over for obvious reasons. 1983/84, promotion season.....
Didn't enjoy Mourinho's other two title wins as much. 05/06, the title was never in doubt but hated that if we went 2-0 up in say the first 10 minutes, it was boring keep ball for the rest of the game. Although that season, I always enjoyed Crespo's goal celebrations. The title win when Mourinho came back, was fantastic until the Spurs 5-3 loss after which he pooped himself and it was a dull affair till the end of the season. Obviously, Mourinho knew what had to be done, but in terms of favourite seasons, they are below the others....