Despite qualifying for Europe's premier competition 15 seasons in succession,
Arsene Wenger's men have failed to do what Roberto Di Matteo's
Since then, the Italian has continued an expensive rebuilding process that has taken Chelsea to the top of the spending league as well as the Premier League.
Roman Abramovich has invested over a billion pounds since taking over in 2003, and now his dream of having a successful and attractive side is starting to come true.
Having won the Champions League through some dogged defensive displays, Di Matteo has signed the sort of players that would make Wenger purr; Eden Hazard, Oscar, Victor Moses and Marko Marin.
The latter made his debut in Tuesday's Captital One Cup stroll past what was effectively a Wolves reserve side, along with Brazilian teenager Lucas Piazon and Spanish full-back Cesar Azpilicueta.
All have the flair and ability to complement Juan Mata, still the playmaker in a side that has more attacking midfielders than any other in the country.
Marin might be considered a shoo-in for any other team, but is acutely aware of the competition for places at Chelsea: "It's good, you need that in a top club. If you want to win the Champions League again and the Premier League, you need a lot of quality players."
Their toughest test in the league so far will be at
"It is a derby, and we are up against two German players. He (Podolski) has scored a few goals and he is playing well, but I have not spoken to him recently. We know each other from the national team, of course, but we are not really friends. I talk more with Per Mertesacker."
Much as Marin admires Podolski, he believes Branislav Ivanovic will keep him quiet.
"It will be very hard for Lucas to play against him. Brana is one of the best defenders in the league. I am not sure that Arsenal have played against a good team like us, the Champions League winners.
"From last year to this, Chelsea have changed a lot. Now we have more attractive, offensive players, and I hope we can have a successful time, like last year.
"We hope there will be lots of goals in this team now. For every player it is enjoyable to play in a team like this."
Marin is close to full fitness after a pre-season injury, and added: "When the team is playing well when you come in, you feel better, everybody feels good, and it is easier to play."