Following Sacchi's departure, he won a second Serie A title under replacement manager Fabio Capello during the 1991–92 Serie A season, as Milan won the title undefeated, but persistent knee injuries and competition from youngster Demetrio Albertini limited his playing time, and eventually forced him into premature retirement at the end of the season, at the age of 33.
He played the final match of his career with the club in a 4–0 home win over Hellas Verona on , in which he came off the bench in the final 20 minutes of the game and scored two goals, and was given an ovation by the fans.
Nicknamed Carletto, Ancelotti played as a midfielder and began his career with Italian club Parma, helping the club to Serie B promotion in 1979.
With the new attacking partnership of Enrico Chiesa and Hernán Crespo, Parma finished second in Serie A during the 1996–97 season under Ancelotti, which guaranteed them a place in the next edition of the UEFA Champions League.Ancelotti is the only manager to have won the UEFA Champions League three times and reached four finals (three finals and two victories with Milan, and one victory with Real Madrid).He is also the first manager to have won the FIFA Club World Cup with a European clubs.A world-class midfielder, he was known for his leadership and organisational skills and is regarded as one of the best Italian midfielders of his generation.Although he lacked pace, as well as notable physical and athletic characteristics, he was a hard-working, combative and tenacious team-player, who was competent defensively, and who also possessed excellent technical ability, tactical intelligence, vision and passing range, as well as a powerful and accurate shot from outside the area, which enabled him to contribute to his team's offensive play with goals and assists.
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Despite his ability, his career was affected by several injuries, which limited his playing time, and forced his retirement in 1992.As he was often deployed in front of the back-line, as a central or defensive midfielder, a position which allowed him to set the tempo of his team's play after winning back possession, he is regarded as having been the mentor and predecessor of Demetrio Albertini and Andrea Pirlo in the deep-lying playmaking role at Milan.At international level he played for the Italian national team on 26 occasions, scoring once, and appeared in two FIFA World Cups, finishing in third-place in the 1990 edition of the tournament, as well as UEFA Euro 1988, where he helped his nation to reach the semi-finals.As a manager, he has worked for Reggiana, Parma, Juventus, Milan, Chelsea, Paris Saint-Germain, Real Madrid and Bayern Munich, and has won domestic titles in Italy, England, France and Spain.Under manager Cesare Maldini, he was often deployed behind the forwards, or as a second striker, due to his eye for goal.
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