Ironically, it was a trip to Bolton six years ago that enabled Chelsea to elbow their way into prestigious company, when Frank Lampard's two goals secured the 2-0 victory that clinched the club's first league title for 50 years.
Never, since Abramovich transformed the Premier League after buying Chelsea in 2003, have the club been so poorly placed at this stage of the season as they are now. Their worst position has been third, six points adrift of the leaders. Now they are fourth, 10 points off the top.
Oh no: Chelsea are in their poorest position at this stage of the season in Abramovich's reign
And not since 2001-02 have the club failed to qualify for the Champions League. 'It's unthinkable not to play the Champions League, ' said Ancelotti. 'It is very important to maintain ourselves in the first places of the table. We want to play in the Champions League.'
Yet already there are signs, for instance Steven Pienaar choosing Tottenham over Chelsea, that footballers and their agents will no longer necessarily beat a path to Stamford Bridge, meaning the club risk a financial as well as a footballing calamity if they cannot make the top four this season.
Chelsea are already up against it in their bid to break even before 2013, which is essential under the new UEFA Financial Fair Play rules. Miss that target and they will be excluded from future Champions League competitions. And miss it they will if they cannot even qualify for the Champions League this year.
Chelsea and all clubs must have reduced their losses to at least £19million a year on average over the next two seasons to qualify for the Champions League. The club believe that, despite losses of £44.4m in 2008-09 and similar losses expected to be announced in the next few weeks for the 2009-10 season, they can make the deadline and break even by 2013, and some of the commercial deals they have signed indicate they are right.
Fall of Roman's empire? Abramovich (right) has seen his side's fortunes wane under Carlo Ancelotti (left)
However, that projection is based on the assumption that Chelsea qualify for the Champions League next year and the year after. If they cannot, then all their financial planning will go awry.
Chelsea insist that should Ancelotti's 'unthinkable' occur, they would have to find ways of bridging the financial gap, by seeking extra sponsors and commercial deals more aggressively and selling the naming rights to Stamford Bridge.
Yet it is hard to see how a £35m hole in the accounts could be filled in time for UEFA's new rules. And naturally, exclusion from the 2013-14 Champions League, assuming the club qualified, would exacerbate any decline.
Ancelotti is unlikely to need to worry about the club by then, as it still looks as though he and Abramovich will be parting ways at the end of the season. Chelsea deny that Ancelotti was marginalised during the failed negotiations for Pienaar, insisting that the player was offered the chance on several occasions to meet the manager.
How the mighty have fallen: Last season's double-winners are struggling even to finish in the top four
But chairman Bruce Buck led the negotiations and also offered the player the chance to speak to controversial assistant coach, Michael Emenalo, as well as Paul Clement. That might have been interpreted as undermining Ancelotti, given that Emenalo was promoted on the order of directors after the sacking of Ray Wilkins, despite the fact that he lacks the coaching qualifications for the job.
However, it is said that the meetings with Emenalo and Clement were only raised at the very end of negotiations, after several offers had been made to set up a meeting with the manager, which had been declined by Pienaar's camp.
Nevertheless, Ancelotti had to explain himself at the end of last week, when he initially gave the impression that he, as manager, did not want to sign Pienaar. 'I didn't search for Steven Pienaar to come here to play for Chelsea because we don't need to have a midfielder,' he said. 'We have a fantastic midfield. We don't need to have these kind of players.'
Rejection: Steven Pienaar chose to join Tottenham ahead of Chelsea when leaving Everton
Ancelotti then attempted to clarify that statement. 'If there was a possibility to improve our position in midfield we could think about this. Pienaar is a good player, but he chose Tottenham. I didn't have a problem with the negotiations of the club. I think there are lots of players who will come here. But we don't need this player.'
It does appears that Ancelotti is still being consulted on transfers, as was Claudio Ranieri in his dying days under Abramovich. But his voice rarely seems to be the loudest. And publicly he has always been supportive of his superiors, even to the extent of backing their decision to axe Joe Cole, Michael Ballack, Deco, Juliano Belletti and sell Ricardo Carvalho, despite lining up only Yossi Benayoun and Ramires as replacements.
'Our philosophy was that, because a lot of players were at the end of their contracts, we would change our ways and it was an opportunity for the young players to come in,' said Ancelotti, although now some of those young players, such as Gael Kakuta, are being considered for loans.
'That was the reason. Our philosophy and idea was to change and now we have to wait to see if it was a good or bad idea. But we had all agreed to change this direction.'
The problem is that it has increasingly looked to be a bad idea for some weeks now. If so, and the Champions League ceases to be an annual experience, then, as Liverpool are discovering, the downward spiral often comes quicker than can be imagined.
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