Two semi-final defeats by Liverpool and one by Monaco have left a sour taste in the mouth of the owner and another European near-miss would be hard to swallow.
Manager Jose Mourinho retains all his old confidence but knows the pressure is on to deliver, not just trophies, but crowd-pleasing football.
Last season his squad was blighted by injuries to key players although they still managed to win the FA Cup and League Cup and go close in Europe and the league.
While reclaiming the Premier League crown is possibly Mourinho's top priority, he will ultimately be judged on whether he can bring the European Cup to Stamford Bridge for the first time and he may not get many more opportunities.
"There is huge determination to reach the next stage which is certainly reaching the final," chief executive Peter Kenyon said after the draw.
Anything less will be deemed failure by Abramovich who knows he needs to collect the trophy in order to fulfil his ambition of making Chelsea Europe's top club.
France winger Florent Malouda was Mourinho's major summer recruit and the 13.5 million pounds ($27.4 million) capture from Lyon will provide Chelsea with more attacking flair to go with the striking prowess of Didier Drogba.
Experienced Peruvian striker Claudio Pizzaro looks a shrewd piece of business too, taking the strain off Drogba, although Andriy Shevchenko remains very much in the shadows.
Captain and central defender John Terry and midfield goal poacher Frank Lampard give Chelsea an English spine while Joe Cole and Shaun Wright-Phillips offer trickery and raw pace.
There is no place in the squad, at least for the group stages, for Germany midfielder Michael Ballack who is injured and the failure to land Sevilla right back Daniel Alves in the transfer window was a major blow.
The classy Brazilian could have proved the final piece of the jigsaw for Mourinho.
Nevertheless, the ingredients are all there for Chelsea to go a stage further than ever before, but Mourinho has very little margin for error.
They should cruise through the group stage though after being drawn with Rosenborg, Valencia and Schalke and will then be hoping for a little more luck in the business end of the tournament next year.
