One of the favourites of Nils Liedholm who had noticed him with Parma and made him the pivot of Roma side that won a Scudetto and four Italian Cups, Carlo Ancelotti joined AC Milan on the last day of the transfer market in 1987. Arrigo Sacchi’s on-field alter ego, as a full-fledged midfielder he was key to all-conquering Milan. In the year of the first victory of the European Champion Clubs’ Cup he scored an unforgettable long-range goal to Real Madrid. He retired from playing football at 33 years of age due to knee problems, with a memorable brace against Verona.
