Left wing: Cristiano Ronaldo
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Mourinho's time at Real Madrid was just as contentious as his most recent spell at Old Trafford. Whilst results did not disintegrate to the extent they did at United, Mourinho had a fraught relationship with the Spanish media, substantial sections of the Bernabeu, and many on his playing staff.
Sergio Ramos and Iker Casillas are two of Spain's greatest ever players, who did not make this XI in part because of their combustible relationship with Mourinho. Cristiano Ronaldo was another who clearly did not see eye-to-eye with Mourinho, but there must have been some recognition that the pair needed one another.
Mourinho delivered the first league title Ronaldo won in Spain (which he has only won once since). For his part, Ronaldo's performances for his Portuguese countryman were consistent with the rest of his career — more than a goal in every game.
Striker: Didier Drogba
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With the five-man midfield he frequents, Mourinho tends to search for a one-man army to lead the line. Diego Costa stamped, scratched and booted his way through Premier league center-halves on his way to 20 league goals for Mourinho, a total Diego Milito bettered in the treble winning season.
And while he also used Karim Benzema and Samuel Eto'o, no one represents the archetypal Mourinho striker quite like Didier Drogba. The man for the big occasion, Drogba has a record of 10 goals in 10 finals, scoring the winner in the 2007 FA Cup final for Mourinho, as well as winning two League titles.
A complete forward, who was equally adept at bringing others into play as he was at scoring goals himself, Drogba racked up 71 assists in his time at Chelsea. He is undoubtedly one of the all-time great Premier League strikers, and would flourish in this lineup.