Ancelotti was sacked by Chelsea on Sunday less than two hours after his side concluded a disappointing season with a 1-0 defeat at Everton.
The Italian was dismissed before boarding the team bus back to Manchester Airport, but his fate was effectively sealed by another departure on November 10.
On that day, Ancelotti was still digesting a 2-0 defeat at Liverpool when he was summoned to hear the news that Blues owner Roman Abramovich had dismissed Wilkins and installed the inexperienced Michael Emenalo as his new number two.
Although Wilkins has never given his version of events, it is believed Abramovich decided to wield the axe after the former Chelsea midfielder had questioned the Russian billionaire's right to debate playing matters with the club's management.
Wilkins' cheerful manner had made him popular among Chelsea's players, especially key English players like John Terry and Frank Lampard, and his departure was a clear challenge to Ancelotti's authority.
With Wilkins gone, Chelsea's results crumbled spectacularly.
After losing to Liverpool the reigning champions still had a two-point lead over second-placed Manchester United but that advantage was squandered by a miserable run of just one win in nine league games.
It didn't help that injuries and illness left Ancelotti without the likes of Didier Drogba, Lampard and Michael Essien for long spells.
The club's decision to jettison a host of experienced internationals like Michael Ballack and Joe Cole during the close-season came back to haunt Ancelotti as their younger replacements were painfully exposed.
A 3-0 home defeat against Sunderland was particularly embarrassing and when Arsenal beat Chelsea 3-1 on December 27 it was hard to imagine the Blues would mount any sort of challenge to retain their title.
Ancelotti talked repeatedly of expecting his team's "bad moment" to end, but they continued to squander points to such an extent that they were 15 points behind United by the time they hosted the leaders on March 1.
A controversial 2-1 victory over Sir Alex Ferguson's side in that match acted as the springboard for a late winning run that briefly reignited dreams of retaining the title.
But even the costly signings of Fernando Torres and David Luiz during the transfer window couldn't completely transform Chelsea's season.
Ancelotti was further undermined by the team's Chelsea's tame Champions League quarter-final exit against United.
He had been brought to Chelsea in large part because of his impressive European track record at AC Milan, where he won the Champions League in 2003 and 2007.
But Abramovich and his aide Eugene Tenenbaum had called Ancelotti to a meeting after that loss and accused him of ruining the team assembled at such expense by the owner.
After that dressing down, the former AC Milan coach was a dead man walking when Ferguson's beat the Blues 2-1 in what was effectively a title decider at Old Trafford on May 8.
By now Ancelotti had the air of a man who knew his time was up and he talked openly about the possibility that Abramovich would sack him at the end of the season.
In the end it was only the rather brutal timing of Ancelotti's sacking so soon after the Everton match that came as a surprise.
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