The Blues were on the brink of exiting the Champions League at the hands of Napoli, faced a tricky cup replay at Birmingham City and had slipped out of the top four after losing at West Bromwich Albion in what turned out to be Villas-Boas’ final game.
Yet, just 55 days later, Villas-Boas’ temporary replacement Robert Di Matteo has maintained his former side’s push for fourth in the Premier League, won a place in the FA Cup final and, most resoundingly of all, the Champions League final.
But will this be enough for him to secure the job full-time?
Under Di Matteo, Chelsea have won 10 of 15 matches – a distinctly better run than under Villas-Boas.
However, it is important to put these results in perspective. In the league, all of Chelsea’s victories have come against sides lurking much lower down.
When they have been pitted against sides such as Tottenham Hotspur, Arsenal and even Fulham, they have hardly exuded the flair many would associate with the Londoners.
Martin Jol’s side were more than equal to the task when they met at Craven Cottage.
Often Chelsea have seemingly been happy to grind out goalless draws against their London rivals higher up the table, too.
These are results that hardly inspire confidence for next season.
The Blues’ aggregate victory at Camp Nou on Wednesday night has led many to call for Di Matteo’s instatement as head coach regardless of the result on 19 May in the Champions League final.
The victory continued Barcelona’s poor run against the Blues in the last decade and exemplified Chelsea’s battling spirit once again under their interim coach.
Di Matteo was heralded as tactical magician after Chelsea played for fifty minutes with only 10 men after John Terry’s sending off.
The remaining nine outfield players soaked up the relentless Barcelona attacks orchestrated by Lionel Messi, Andrés Iniesta and Xavi.
However, how much strategic nous is needed to set up two defensive lines of four entrenched in their own half?
This was the formation that Chelsea were forced to adopt with Didier Drogba again playing as an auxiliary midfielder – a position he takes with regularity these days when his team is in possession of a slender lead.
It is important though not to take anything away from a famous victory for the Blues against, arguably, the best club side in European history.
But it was a result that contained a large degree of fortune rather than inspirational decision-making from the touchline – and how that fortune was needed with the side reduced to 10 men against the might of Barcelona.
Many would argue that Di Matteo can perform the role of an interim coach, as he has proved, but does not have the capability and experience to take on the job full time.
Ahead of him lies the tricky task of re-sculpting and re-invigorating the Chelsea squad, heavyweight with players from the José Mourinho era who, despite their talent, are making it difficult for the club to take a new direction.
Roman Abramovich will, no doubt, give Di Matteo the position on a full-time basis should Chelsea go one better against Bayern Munich next month.
The much sought-after Champions League trophy will finally be the Russian oligarch’s possession eight managers and more than a billion pounds after assuming control in 2003.
But if Di Matteo fails, where will Abramovich go next to find the man who will create a Chelsea fit to keep its place as one of the leading English teams?
There may not be time for Di Matteo to grow into a job that needs diplomacy and experience by the bucket load. And then Abramovich’s hand will be forced.
MORE: Man United latest news
MORE: Arsenal latest news
MORE: Chelsea latest news
MORE: Liverpool latest news