Carlo Ancelotti, who, as a player, was known as "Carletto," appeared 26 times for Italy, and participated in the 1986 and 1990 FIFA World Cup, where he was teammates with former club mate and former Italy coach Roberto Donadoni, former Inter Milan coach Roberto Mancini and a young Paolo Maldini.
He started his club career in 1976 with Parma A.C.. In 1979, he transferred to AS Roma, as captain and midfielder, where he won the Italian championship (1983) and four times the Italian Cup. From 1987 until 1992 he played for A.C. Milan and was part of the Milan squad that won consecutive European Cups in 1989 and 1990.
During this time, Milan played with one of their finest teams ever assembled in that decade, with Maldini, Franco Baresi, Mauro Tassotti, and Alessandro Costacurta in defence, Frank Rijkaard, Ruud Gullit and Roberto Donadoni in midfield and Marco van Basten in attack.
Ancelotti is one of only six coaches to win the Champions League as both a player and a coach. Ancelotti's first coaching job was with Serie B squad A.C. Reggiana 1919 in 1995. In his only year with the club, Reggiana earned promotion to Serie A. Ancelotti then returned to Parma—which included upstart goalkeeper Gianluigi Buffon and current Milan goalkeeping trainer Villiam Vecchi—in 1996.
He became the successor of Marcello Lippi at Juventus the next season, but went trophyless during his two-year stint, finishing runner-up twice in Serie A.
Ancelotti's fortunes changed when he went to AC Milan in 2001 as a replacement for the fired Fatih Terim. He was inheriting another recently trophyless team in Milan, as the Rossoneri had floundered domestically and in Europe since their last Scudetto victory in 1999.
In his first full season, Ancelotti soon had Milan back in European competition, leading them to the semi-finals of the 2001-02 UEFA Cup, in which Milan finished third.
His Record in Milan was as following:
UEFA Champions League
UEFA Super Cup
FIFA Club World Cup
On May 31, 2009 Ancelotti announced his resignation from Milan less than an hour following their 2-0 victory over ACF Fiorentina. The next day, he was confirmed as the new Chelsea manager after agreeing to a three-year, £9-million contract. He was the fifth Chelsea manager in about 21 months.
As Ancelotti's record shows that he has just won Coppa Italia & Serie A just one in eight years and as we know Roman Abramovich, Ancelotti's future in Chelsea is looking dark.