A former Milan midfielder, nicknamed 'Carletto,' Ancelotti appeared in Italia 90 as the hosts reached the World Cup semi-finals and ultimately won 26 caps with the Azzurri.
While Ancelotti may have been regarded as an unspectacular player, one surrounding by the more eye-catching talents of Roberto Baggio, Franco Baresi and Paolo Maldini, he can claim to hold his own with any of his rivals in the managerial arena.
Having started out as a coach with Reggiana in 1995, Ancelotti secured promotion from Serie B in his only season at the club. That success prompted Parma to appoint him as coach and his three-year reign saw him deliver the Uefa Cup as the club grew into a genuine force in Italian and European football during the mid-1990s.
But while Parma's success saw the club grow into a respected force, the leading lights of Italian football remained the traditional powerhouses of Juventus, Milan and Internazionale and, when Marcello called time on his reign as Juve coach in 1999, Ancelotti accepted the role of coach at Italy's most successful club.
His two years in Turin proved unsuccessful, however, with two runners-up positions in Serie A the sum total of his efforts.
Milan proved to be his salvation, however, and having arrived at the San Siro with the rossonerri struggling to reproduce their glory days under Arrigo Sacchi and Fabio Capello, Ancelotti transformed the club and brought the success back, both domestically and in Europe.
In his first season, he guided Milan to the Uefa Cup semi-finals and fourth spot in Serie A, but his defensive tactics prompted criticism from club owner Silvio Berlusconi.
Ancelotti remained loyal to his principles, though, and he won he Champions League in 2003 with a penalty shoot-out victory over Juventus at Old Trafford. A year later, he guided Milan to his only Serie A title as coach at the San Siro.
The Champions League final defeat against Liverpool in Istanbul in 2005, when Milan threw away a 3-0 half-time lead before losing on penalties, proved a low-point, but that defeat was avenged with a 2-1 victory over Rafael Benitez's team in the Champions League final in Athens two years later.
Eight major trophies were won by Ancelotti during his eight years at San Siro, a success rate that has prompted Roman Abramovich to tempt him to Chelsea on a three-year contract.
Ancelotti is viewed as a calm operator who rarely betrays emotion on the touchline. He has a track record of managing the biggest personalities at Milan, however, so the Chelsea dressing-room will be nothing new to him.
Carlo Ancelotti factfile:
1959: Born in Reggiolo, Italy on June 10.
1976: Begins professional playing career with Parma.
1979: Joins Roma. 1980: Wins Coppa Italia with the Giallorossi.
1983: Part of the Roma side that wins the Serie A title.
1984: Does not feature as Roma lose to Liverpool on penalties in the European Cup final on their home ground.
1987: Joins AC Milan. 1988: Milan win the domestic title in Ancelotti's first season at San Siro.
1989: Part of the Milan side which wins the European Cup, beating Steaua Bucharest 4-0 in the final.
1990: Milan retain European title with a 1-0 win over Benfica. Ancelotti is part of the Italy squad for the
1990 World Cup.
1992: The Rossoneri win the Italian league title. Ancelotti retires from playing.
1995-96: Takes up his first coaching post with Serie B side Reggiana. Leads the side to promotion to the top flight, before leaving to join Parma.
1996-97: Leads Parma to second place in Serie A.
1998: Appointed manager of Juventus.
2001: After a fifth-place finish in his first season at the Stadio delle Alpi, steers Juve to consecutive second-place finishes.
2001: November - Appointed manager of AC Milan.
2003: Manages Milan to Champions League glory as they beat Juventus on penalties in final at Old Trafford.
2004: Leads Milan to Serie A title.
2005: Milan let a 3-0 lead slip to be pegged back to 3-3 by Liverpool in the Champions League final in Istanbul. The Reds win on penalties.
2006-07: Milan begin the season docked eight points for their part in the 'calciopoli' match-fixing scandal.
2007: Gains his revenge on Rafael Benitez as Milan beat Liverpool 2-1 in the Champions League final in Athens.
2008: Pressure mounts on Ancelotti as Milan bow out of the Champions League in the last 16 to Arsenal and fail to finish in the top four of Serie A.
2008: May - Milan rebuff a reported approach from Chelsea to talk to Ancelotti about succeeding Avram Grant.
2009: May 31 - Ancelotti confirms his contract with the club has been mutually terminated. He denies, however, that he has agreed a deal with Chelsea. June 1 - Confirmed as new Chelsea manager on a three-year contract.