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He is regarded as one of the greatest defenders of all time. Maldini held the record for appearances in Serie A , until he was surpassed by Gianluigi Buffon in Maldini spent all 25 seasons of his playing career in Serie A with Milan and retired at the age of 41 in Following his retirement, Milan retired his number 3 shirt. Maldini made his debut for Italy in and played for 14 years before retiring in with 7 goals and caps. He held the record for appearances with Italy, until he was surpassed by Fabio Cannavaro and Gianluigi Buffon.
Maldini captained Italy for eight years and held the record for appearances as Italy's captain 75 , until he was again surpassed by Cannavaro and Buffon. Although he did not win a tournament, he reached the final of the World Cup and Euro and the semi-final of the World Cup and Euro He was elected into the all-star teams for all of these tournaments.
He also came third in the Ballon d'Or rankings in and In , at the age of 10, Maldini had his first tryout for AC Milan youth academy. Prior to that, he had only played street football.
He successfully played the test game as a right midfielder or winger in the 4β4β2 formation and was accepted into his age group's squad. 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 β85 season , and he made his league debut for Milan under manager Nils Liedholm during the same season on 20 January , replacing the injured Sergio Battistini in a match against Udinese at age The β88 Scudetto under Arrigo Sacchi marked Maldini's first trophy, and the first of seven league titles, with the club.
Maldini went on to win the Supercoppa Italiana with Milan the following season, and followed up this trophy with back to back European Cup titles in β89 and β90 , while Milan finished in third and in second place in Serie A during those respective seasons. Milan reached the final of the β90 Coppa Italia , losing out to Juventus. Milan also managed to capture successive European Super Cup titles in and , as well as successive Intercontinental Cup titles, once again and The following season, in Sacchi's final season with the club, Milan were eliminated in the quarter-finals of the European Cup by eventual finalists Marseille , and finished second in Serie A , behind Sampdoria , once again with the best defence in the league, conceding only 19 goals.