However, after reaching the knockout stage with a game to spare, the Blues then blew the chance to progress as one of the seeded sides by drawing 1-1 at home to Atletico Madrid on Tuesday night, thus allowing Roma to nick top spot in Group C.
Essentially, that would mean a 67 per cent chance of a terrible draw. Chelsea fans will not like those odds.
Of course, it was the one point accrued from two games against Roma that proved most costly but Chelsea would still have taken top spot had they seen off Atletico at Stamford Bridge. Instead, they drew 1-1 - despite creating a host of chances.
They could even have lost. Former Chelsea striker Fernando Torres beat Davide Zappacosta to a corner whipped in to the near post, leaving the unmarked Saul Niguez - Tiemoue Bakayoko had completely lost his man - with an easy header to put the visitors a goal to the good.
Unsurprisingly, it was Eden Hazard who dragged the Blues back into the game. The Belgian created some space for himself with some trickery on the edge of the box before unleashing a low drive that deflected in off Stefan Savic.
In truth, an own goal was probably the only way that Chelsea were going to beat Jan Oblak, who produced a string of sensational saves on the night.
Chelsea could - and perhaps should - have forced a winner, with Willian having recorded the miss of the game not long after being sprung from the bench.
Consequently, Blues boss Antonio Conte will be both frustrated and annoyed that his side failed to top a group that they had taken complete control of with a thrilling and deserved win over Atletico in Madrid on matchday two.
However, the loss of N'Golo Kante to injury ultimately proved their undoing, with the Frenchman's absence having been sorely felt in a 3-0 loss in Rome, after Chelsea had been fortunate to nick a draw in the home fixture a couple weeks earlier.
Against Atletico, the Blues were ultimately punished for their profligacy. They had 17 shots on goal - Alvaro Morata had seven of them - but they failed to claim all three points. A European heavyweight could now be waiting for them in the last 16.
Chelsea, of course, will fear nobody. This, after all, is still the same side that won away to Atletico. In their return to the Champions League, they have come out of arguably the toughest group in the competition.
As Hazard enthused afterwards, "We are a top team, so we can face any team. We know PSG and Barcelona are very good but we are Chelsea so we have to be ready for everything. We can do everything!"
If next Monday's draw is unkind, Chelsea fans will be hoping he's right!