Chelsea face Real Madrid in the International Champions Club Final, which has a very interesting touch to it.
Both these high-profile managers have been in charge of the opposite club. They both led the other clubs to victories and championship titles, and also had a controversial ending.
Also common is a disastrous star player signing, in the form of Fernando Torres for Chelsea under Ancelotti and Kaka to Real Madrid under Mourinho.
While the Special One left the Real Madrid job last season after an up and down three years, Ancelotti was sacked from his Chelsea job after the 2011 season having managed the Blues for two seasons.
Mourinho, who was expected to revolutionise the Bernabeu outfit and usher a new era of dominance for the Spanish giants, had a decent run but a list of controversies saw his stay shortened.
He had a very notorious falling out with club Captain Iker Casillas, outbursts with star player Cristiano Ronaldo, Sergio Ramos and others, and failed to justify his big name signings like Kaka and Luka Modric.
Towards the end of last season, he also fell out with the Spanish media and the Real Management, which was the final nail in the coffin.
Ancelotti was sacked by Chelsea's ruthless owner Roman Abramovich after he failed to win a trophy in 2011. He however, had a good relation with most players and fans alike, and remains widely respected by the Blues.
Under him, Chelsea claimed their first domestic double in 2009/10, but a large sore point in his tenure would be the British record signing of Torres from Liverpool, which has repercussions even today.
While one man would want to defeat his rival, to prove his critics wrong, the other would want to show what they missed by firing him.
Many of the Real Madrid players who were happy to see the back of Mourinho would be wanting to clinch this victory against their former manager.
The Blue brigade would, on the other hand, want to win this for their new boss, a man on whom a lot of hopes and dreams now depend.
The tension would be high, the emotions loud, and although both teams may not consider the tournament that high up the pecking order, egos will be at stake.
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