The only thing Chelsea's 2 titles highlight is that we haven't won enough to match our stature in the game.
If it weren't for the Munich tragedy, the babe's with Best and Law still joining later hopefully, would have easily won 4/5 between 58 - 68 in my opinion.
Fergie was hindered pretty badly by the foreign player rule in the early to mid 90s but the Milan team of that time was insane so it probably wouldn't have mattered anyway.
We then had pretty rotten luck early to mid 00's often being beaten by the eventual winner or finalist. Overall, our tactics in the 90's to early 00's were probably too naive, probably due to the fact that we were completely dominating domestically.
From 2007 onward, Fergie had mastered his tactics in Europe and this is the period which still haunts me most. I have extreme anger towards the Glazers from the years 09-13 and have disliked them since.
3 Finals in 4 years was phenomenal and I can't be too annoyed about only winning 1 as that Barca team was so exceptional, it was just unfortunate that arguably our greatest team since the late 60's had to go up against one of the greatest teams of all time.
The Glazers 09-13 were absolutely appalling though and that is the period which set us up for a decade of failure. Losing one of the all time greats in 09 and replacing him with Valencia and Owen, it still pains me to reminisce. World record £80 million received and not even £20 million reinvested. Tevez, a fantastic player in his own right was allowed to be signed by a direct rival. To make matters worse Robben and Sneijder were available this window for a combined 40 million Euro, not even half of what we got for Ronaldo. Christ , even thinking about it, I still get angry.
Over the next few seasons we'd stand by and watch as the likes of Aguero, Kompany, Silva, Mata, Matic, Hazard and Toure were being signed by our direct competition while we signed the likes of Smalling, Jones , Bebe and Young.
Robben would go on to Brutally knock us out of the CL in 2010 when he should have been playing for us. The Glazers robbed both ourselves and Fergie of 2 more CL titles in this period. If we'd have at least replaced Ronaldo and Tevez with Robben and Sneijder we'd have lifted the title in 2010 and 2013.