1978–1987: Youth career, AC Milan senior debut and early professional career In 1978, at the age of 10, Maldini had his first tryout for
AC Milan youth academy. Before that, he had only played
street football. He successfully played the test game as a
right midfielder or winger in the 4–4–2 formation and was accepted into his age group's squad. He would continue playing in this position until the age of 14, when he was moved to right
full-back. Due to him being good on the ball with both of his feet, he would sometimes be fielded on the left side as well. Maldini won the
Coppa Italia Primavera with the Milan Youth side during the
1984–85 season, and he made his
league debut for Milan under manager
Nils Liedholm during the
same season on 20 January 1985, replacing the injured
Sergio Battistini in a match against
Udinese at age 16. It was his only league appearance of the campaign, but he was immediately made a member of the starting eleven the
following season, at age 17, at right-back, being handed the number 3 shirt, which had previously also belonged to his father, Cesare. Maldini also made his
Coppa Italia debut in 1985, on 21 August, while his debut in European competition also came later that same year, on 18 September. in a 1–0 win against
Como.
1987–1991: Domestic and international success with The immortals The
1987–88 Scudetto under
Arrigo Sacchi marked Maldini's first trophy, and the first of seven league titles, with the club. Nicknamed "The Immortals", Sacchi's Milan side is remembered for including the Dutch trio of
Frank Rijkaard,
Ruud Gullit and
Marco van Basten, as well as the Italian midfielders
Carlo Ancelotti,
Roberto Donadoni (and later
Demetrio Albertini), and a strong defensive lineup. Under Sacchi and later
Fabio Capello, Maldini formed with long-timers
Franco Baresi,
Alessandro Costacurta,
Mauro Tassotti, as well as
Filippo Galli,
Stefano Nava and later
Christian Panucci, one of football's strongest defensive quartets of all time. During the 1987–88 Serie A season, Milan only conceded 14 goals, finishing with the best defence in Italy, as they went on to win the Serie A title. Maldini went on to win the
1988 Supercoppa Italiana with Milan the following season, and followed up this trophy with back to back
European Cup titles in
1988–89 and
1989–90, while Milan finished in third and in second place in Serie A during those respective seasons. This championship was Milan's first of three consecutive Serie A titles under Capello in the early 1990s. Maldini helped Milan defend the
Serie A title the following season, and reach the first of three consecutive
UEFA Champions League finals. Milan lost the
1993 Champions League final in a 1–0 defeat to Marseille. That season, Maldini scored his first goal in
European Competitions on 21 October 1992 in a 1–0 Champions League win against
Slovan Bratislava, After winning his third Champions League title and reaching the
1994 World Cup final, Maldini became the first defender ever to win
World Soccer magazine's annual
World Player of the Year Award. During his acceptance speech, Maldini called his milestone "a particular matter of pride because defenders generally receive so much less attention from fans and the media than goalscorers. We are more in the engine room rather than taking the glory". He then singled out Milan captain Franco Baresi as a player who "really [deserved] to receive the sort of award I have received". The following season, Maldini lined up with
Alessandro Nesta, Alessandro Costacurta and
Cafu, who, along with
Jaap Stam during the
2004–05 season, formed a formidable defensive lineup in Italy and in Europe. Milan finished third in
Serie A, but Maldini won the first
Coppa Italia of his career, defeating Roma in the final. He and his father are only one of three other father-son pairs to have also done so; the others being
Manuel and
Manolo Sanchís of
Real Madrid, and
Carles and
Sergio Busquets of Barcelona. Maldini was elected
Man of the Match and was named in the
UEFA Team of the Year for the first time in his career. Maldini was also included in the
FIFA 100 list in 2004, which was a selection of the 125 greatest living footballers, chosen by
Pelé. Following his Series A-winning performances, Maldini was elected to be the
Serie A Defender of the Year in 2004 at the
Italian footballing Awards. seven days earlier, he had played his 800th game in all competitions for Milan. That season, Maldini captained Milan to their third Champions League final in six years, leading them to a 2–1 victory over Liverpool in the
final on 23 May 2007 in
Athens, avenging their defeat from 2005. At age 38, Maldini became the oldest captain to lift the Champions League trophy. Maldini participated in eight Champions League finals during his career, which is equalled only by
Francisco Gento of Real Madrid; Maldini lifted the trophy five times, twice as captain. In an interview with
ESPN aired prior to the 2007 final, Maldini labeled the 2005 Champions League final as the worst moment of his career. A match where he scored the fastest-ever goal in a European Cup final after 51 seconds and became the oldest player ever to score in a final, Milan lost on penalties to Liverpool after leading 3–0 at half-time. Maldini was elected the
UEFA Club Defender of the Year for his 2007 performances. Following Milan's elimination from the Champions League by
Arsenal in March, however, Maldini stated that he would possibly delay his retirement for at least a further year. He signed an extension on 6 June that kept him at Milan for the
2008–09 season.
2008–2009: Final years and retirement On 16 February 2008, in a match against Parma at the
Stadio Ennio Tardini, Maldini came on for defender
Marek Jankulovski to make his 1,000th professional career appearance, of which 861 were with Milan, 12 with the
Italy under-21 side, 1 with the Italian Olympic team and 126 with the
Italy senior team. In European football, only the English goalkeeper
Peter Shilton had collected more appearances at the time: 1,390 between 1966 and 1997. Maldini played his last game in the Champions League on 4 March 2008, a 2–0 loss at the
San Siro in the last 16 against Arsenal which eliminated Milan from the
2007–08 Champions League. In 2008, Maldini was awarded the
FIFA Order of Merit, as well as the Premio Internazionale
Giacinto Facchetti, which is awarded to a player who was demonstrated both skill and fair play throughout his career. On 18 April 2009, Maldini announced that he would retire at the end of the 2008–09 season. His last appearance for Milan, and his last game as an active player, was a 2–0 win against Fiorentina on 31 May 2009 in the last match of the Serie A season. This win meant Milan finished in third place and qualified for the following season's Champions League. Maldini was once again given a standing ovation by the fans. As they had previously done with Franco Baresi's number 6 shirt, Milan
retired Maldini's number 3 shirt, but stated that it will be bequeathed to one of his sons if one of them were to make the club's senior team. On 28 August 2009 in
Monte Carlo, Maldini was awarded a prize for his career by
UEFA during the draw for the group stage of the
2009–10 Champions League. On 17 November 2009, Spanish sports newspaper
Marca awarded Maldini the "Marca Leyenda" prize for his career and achievements. ==International career==