[4] One of his sons, Paolo, also had a successful football career as a defender with Milan,[5] and also once held the record for the most caps for the Italy national team (now third behind Gianluigi Buffon and Fabio Cannavaro).

[8][9][10] Maldini began his playing career with local side Triestina, in 1952,[4] and made his Serie A debut in his first season with the club, on 24 May 1953, in a 0–0 away draw against Palermo.

[11] After two seasons with Triestina, Maldini transferred to AC Milan in 1954, where he went on to achieve notable successes both domestically and internationally in the team's starting line-up, also becoming an important figure at the club.

[12] He made his debut with the club on 19 September 1954, in a 4–0 league win over his former side, featuring in a Milan team which included several important players at the time, such as Lorenzo Buffon, Francesco Zagatti, Nils Liedholm, Gunnar Nordahl, and Juan Alberto Schiaffino; he immediately broke into the first team and won his first league title in his debut season with the squad.

[13][15] Maldini won four league titles with Milan, and also later became the team's captain in 1961, a role which he held for five years, until he left the club, and was succeeded by Gianni Rivera.

[4][5][14][15][22][23] Despite his reputation as a consistently world-class defender, in his early career Maldini was at times also known for being overly confident in possession, and for having a penchant to take risks when carrying or playing the ball out of the defence, due to his passing accuracy and ability on the ball; this tendency occasionally led to sporadic and atypical defensive errors, which were later humorously dubbed Maldinate by the Italian media.

[8][22][26] Maldini took charge of the Italian Under-21 side in 1986, and coached the team for ten years, winning the European Under-21 Football Championship tournament a record three consecutive times between 1992 and 1996.

[32] Despite initially struggling in qualification, the Italian media and fans had great expectations of the 1998 side, which included a strong defence, and several prolific attacking players, such as Christian Vieri, Alessandro Del Piero and Filippo Inzaghi, among others, in their prime.

[37] Although Italy did not lose a match at the World Cup, Maldini resigned after the tournament due to heavy criticism in the Italian media over his allegedly ultra-defensive and "old-fashioned" catenaccio-inspired tactics, which included the use of a traditional man-marking defensive back-line, as well as a sweeper.

[4][24][26][33][38][39][40][41] He was also condemned for leaving Gianfranco Zola out of the squad, and for his reluctance to field creative forwards Roberto Baggio and Alessandro Del Piero alongside each other in the front-line, opting instead to have one player come on for the other in the second half;[26][33][42] these controversial substitutions were compared to those made between Sandro Mazzola and Gianni Rivera by Ferruccio Valcareggi, the Italian manager at the 1970 World Cup.

[43][44][45] After serving as a head scout for his former team Milan from February 1999,[20] Maldini briefly returned to coach the Milan first team in March 2001, serving as an interim manager for the club (whose captain was his son, Paolo)[46] alongside youth coach Mauro Tassotti, following Alberto Zaccheroni's sacking, and led the squad for their final games of the season.

[47] Although the club endured a disappointing season, finishing in sixth place and failing to qualify for the Champions League, Maldini did lead the team to a memorable 6–0 victory over cross-city rivals Inter in the Milan Derby on 11 May;[13] the result was Inter's worst-ever home defeat in Serie A, and Milan's biggest league win in the Derby.

[51] Despite missing Chilavert for the first game due to suspension, Paraguay managed to advance from Group B to the Round of 16, after a 2–2 draw with South Africa,[52] a 3–1 defeat from Spain,[53] and a 3–1 victory over Slovenia.

[nb 1] In attack, he usually paired two forwards who would complement each other alongside one another, namely a traditionally large, physical, and prolific centre-forward – such as Christian Vieri – with a smaller, faster, creative and more technical second striker – such as Roberto Baggio or Alessandro Del Piero.

[79] In his honour, a minute of silence was held before every league game in Italy that weekend, while Milan players wore black armbands in their match against Atalanta.