Not content with winning multiple Serie A titles and European Cup with AC Milan as a player, Carlo Ancelotti repeated the trick as a manager.
The man with football's most expressive eyebrow ended his playing career with a medal-packed five-year spell at the San Siro in 1992, only to return as boss nine years later and spearhead another period of success for the Rossoneri.
Stints at Chelsea, Paris Saint-Germain, Batern Munich, Napoli and Everton have followed, with the 65-year-old currently in his second spell at Real Madrid and was ranked at no.2 in FourFourTwo's list of the best managers in the world last year.
But how much can you remember of Ancelotti's spell as AC Milan boss? We've drawn up a typically fiendish FourFourTwo quiz to test your knowledge of the players, the titles, the awards and more from his time in charge of the Italian giants.
There's no time limit and 10 questions to answer, so take your time and do your best.
Remember to tweet your scores @FourFourTwo and share with your mates.
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