Can the ‘Special One’ triumph or will he be humbled at the San Siro?
Inter Milan against Chelsea is the Champions league's glamour tie, forget about Beckham's return against Manchester United, this showpiece brings Chelsea and the 'Special One' together again.
The whole football fraternity will be fascinated by this clash between two of Italy and England's superpowers.
Chelsea's rise to stardom is mainly due to the impact that Jose Mourinho's tenure had on the club. The current Chelsea team that sit first in the Premier league are still mostly Mourinho's prodigies and are the same players that he turned into winners at Chelsea.
He would now take extra delight in winning against the Blues.
Mourinho who is adored by the Chelsea faithful, managed to win six trophies in three years at Stamford Bridge, including back-to-back league titles. To add to the match's spice, the new Blues boss Carlo Ancelotti is returning to Milan where he used to manage Inter's bitter city rivals, AC Milan until May last year.
Ancelotti and Mourinho have a tempestuous relationship, Mourinho had a slight dig at Ancelotti pre-match stating, 'The Premier League is never easy, every game normally is difficult, but when a team is strong, strong, strong, strong, strong it doesn't lose so many matches, so many points'.
He was referring to Chelsea's inability to finish teams off, they have lost four Premier League games so far this season.
Mourinho loves making enemies. He continually caused a stir at Chelsea and had a love and hate relationship with the media. In Italy he is succeeding beyond his wildest dreams, he has belittled Italian football, claimed referees conspire against Inter and managed to turn the whole Italian media against him.
Away from the blue and black of Milan, Italian media would love to see him humbled.
Abramovich apparently did not dispose of Mourinho at Chelsea because of his inability to win the Champions League, the 'Holy grail'. It was more to do with Mourinho's ill mannered behaviour, he was viewed as 'unmanageable'.
However, Abramovich and Mourinho have patched up their relationship and neither is held in contempt, there is more a feeling of mutual respect. Mourinho had invested Abramovich's endless millions wisely.
Inter certainly have the guts to go to battle against Chelsea, they were reduced to nine men for the second time this season against Sampdoria at home, at the weekend, yet they managed to achieve a creditable 0-0 draw and could have won the clash.
Inter goalkeeper, Julio Cesar is set to play against Chelsea after recovering from a car crash. Lampard should be fit for Chelsea after a virus stopped him playing against Wolves. Essien, A Cole, Bosingwa, and Deco are all long term injury problems for them and will not feature.
I would back Chelsea to come from behind and win or draw at 9/2, Chelsea have often conceded early during this season's matches yet they come back into the game as it progresses, they are a very resilient side and will fight tooth and nail for Ancelotti to get a result at the San Siro. The bet also allows for the draw and the win, should Chelsea fall behind early.
Drogba at 5/4 to score anytime is a fitting price for a player in form, he adores Mourinho but nothing can stop Drogba in his quest for a Champions League medal, after coming so close under Avram Grant's leadership two years ago. He is extremely powerful and if he is motivated for the win, he can be unstoppable.
Ancelotti's sleazy eleven will head to Mourinho's theatre wanting that win, but maybe Mourinho has already found a kink in Chelsea's armory that he can exploit midweek?
However, Ancelotti will feel that he knows Inter very well after his experiences in Italy, it will be a truly tantalising experience for all involved, with many a twist and turn to come.