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Sure, Carlo Ancelotti had a wonderful playing career. The former Parma, Roma and AC Milan midfielder was capped 26 times and won three Scudettos. But, without doubt, the Italian is best known for his managerial exploits. A three-time UEFA Champions League winner, Ancelotti has won silverware in Italy, England, France, Spain and Germany in the hottest of hot seats at Juventus, AC Milan, Chelsea, Paris Saint-Germain, Real Madrid and Bayern Munich. Make no mistake, Ancelotti knows this sport and he knows how to master it.