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
Gigi Buffon and current Milan goalkeeping trainer
Villiam Vecchi - in 1996, and won the 1998-99 UEFA Cup. 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. That all 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 foundered 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. The following season, Ancelotti, who was heavily criticized by club president
Silvio Berlusconi due to his defensive tactics, was able to adopt a creative play in Milan while making several roster changes. He made
Dida, still maligned for his
2000 Champions League howler against
Leeds United, his new starting goalkeeper barely a month into the 2002-03 campaign, while converting budding striker
Andrea Pirlo to a defensive playmaker and playing him alongside
Manuel Rui Costa. At the same time, the striking partners of
Filippo Inzaghi and
Andriy Shevchenko were dominant and dynamic. Milan won the
Champions League, beating Ancelotti's old team, Juventus, 3-2 on penalties at
Old Trafford, and took home the Scudetto and
Coppa Italia in 2004.
Under Ancelotti's reign, Milan were also back-to-back Serie A runners-up to Juventus in 2004-05 and 05-06 (both
Scudetti were later wiped from the record books due to Juventus' involvement in the
Calciopoli scandal), and lost the
2005 CL final in horrific fashion to
Liverpool F.C., in which Milan lost 3-2 on penalties after blowing a 3-0 halftime lead. Two years later, though, Milan
avenged their defeat to Liverpool with a 2-1 win at the Olympic Stadium in Athens on May 23, 2007, leading to Ancelotti's second Champions League trophy as Milan coach and his fourth title overall, having also won it twice as a Milan player in 1989 and 1990. On May 30, Ancelotti signed a two-year contract extension, keeping him at Milan until 2010.
Ancelotti is only the fifth coach to win the Champions League as both a player and a coach, along with
Miguel Muñoz (Real Madrid player 1956, 1957, Real Madrid coach 1960, 1966);
Giovanni Trapattoni (AC Milan player 1963, 1969, Juventus coach 1985);
Johan Cruyff (AFC Ajax player 1971-73, FC Barcelona coach 1992) and former Milan teammate
Frank Rijkaard (AC Milan player 1989, 1990, Ajax player 1995, FC Barcelona coach 2006). He also ranks second in number of Milan matches coached with 322, trailing
Nereo Rocco (459).
He has often expressed interest in coaching
Italy after his Milan contract expires in 2010.
