[22] 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.

[28] 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.

[29] 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.

Maldini helped Milan defend the Serie A title the following season, and reach the first of three consecutive UEFA Champions League finals.

Due to Alessandro Costacurta's suspension and injuries sustained to Franco Baresi, Jean-Pierre Papin and Marco van Basten, Barcelona's "Dream Team", coached by Johan Cruyff, were heavy favourites to win the trophy, with the formidable attacking duo of Romário and Hristo Stoichkov.

[39] Despite their key absences, Maldini helped the Milan defence keep a clean sheet and overcome Barcelona 4–0 in the final, with two goals from Daniele Massaro and one each from Dejan Savićević and Marcel Desailly.

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.

[40] Maldini also placed third in the 1994 Ballon d'Or, behind Stoichkov and compatriot Roberto Baggio, and fifth in the FIFA World Player of the Year Award.

[26][27] Following Capello's departure, and the aging and retirement of several key players, Milan suffered disappointing results during the next few seasons, undergoing several managerial changes.

Milan lost the Supercoppa Italiana to Fiorentina in 1996, and failed to qualify for European competitions for two consecutive seasons, as well as suffering a group stage elimination in the 1996–97 Champions League.

Milan finished second in Serie A to Juventus that season, and reached the Champions League final, only to lose out on penalties to Liverpool, although Maldini opened the scoring in the first minute.

[26][27] The following season, Maldini helped to captain Milan to a fourth-place finish, despite their point deduction, leading them to obtain a crucial Champions League qualifying spot.

[27][56][57] 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.

[27][61][65] In the opening match of the tournament on 10 June, a 1–1 draw against hosts West Germany, he became the youngest player ever to feature for Italy at the UEFA European Championship, at the age of 19 years and 350 days.

Italy eventually placed third after defeating England 2–1 in the third-place final match, and finishing the tournament with the best defence having conceded two goals throughout the entire World Cup.

[64] Maldini was part of the Italy squad that participated in the 1992 U.S. Cup, finishing in second place in the friendly tournament, behind the host nation.

Maldini helped Italy keep a clean sheet in the final against favourites Brazil as the team eventually lost on penalties.

Maldini, partnering with Alessandro Costacurta, Fabio Cannavaro, Alessandro Nesta and Giuseppe Bergomi, also helped Italy to keep clean sheets in the second group match against Cameroon, the round of 16 match Norway and France in the quarter-finals, but Italy eventually went out of the tournament to the hosts and eventual champions on penalties, for the third consecutive time in a World Cup.

[71] The following year, Italy reached the final of Euro 2000, but lost once again to defending World Cup champions France in extra time.

Italy topped their group, winning every match, and Maldini, starting alongside Fabio Cannavaro and Alessandro Nesta, helped the Italian defence to concede only two goals en route to the final, keeping clean sheets against co-hosts Belgium in the group stage, Romania in the quarter-finals and co-hosts the Netherlands in the semi-finals.

He spent over half of his 16 years as an international as team captain, wearing the armband a record 74 times,[75] until he was overtaken by Cannavaro, and subsequently Buffon.

[77] In February 2009, Italian head coach Marcello Lippi declared his support for a testimonial match for Maldini, stating that it would give him a chance to play for the Azzurri for a final time.

Maldini played in the 11th Match Against Poverty on 4 March 2014 alongside other footballers such as Ronaldo, Zinedine Zidane, Luís Figo, and Pavel Nedvěd, which was held in Bern, Switzerland, with the proceeds being donated to the recovery efforts in the Philippines after Typhoon Haiyan.

[84][85] On 1 September 2014, Maldini, along with other footballers, took part in the "Match for Peace", which was played at the Stadio Olimpico, Rome, with the proceeds being donated to charity.

[93] In August 2018, a few weeks after Milan's changed their ownership to Elliott Management Corporation, Maldini accepted an offer to become the sporting director for the club.

He was switched to the left-back position by manager Arrigo Sacchi due to Mauro Tassotti occupying the right side for Milan.

[110][111] In the final few years of his career, as he lost speed, he was moved to a centre-back position, where he excelled in relying on his experience, aerial abilities, and tackling to stop attackers.

[113][114] Despite being a precise tackler and an imposing defensive presence, he often avoided committing to challenges when he deemed them unnecessary,[115] preferring to restrict the offensive play of his opponents through his positioning and man-marking.

[114] With 126 caps for Italy, he held the record for appearances with the national team, until he was surpassed by Fabio Cannavaro in 2009 and by Gianluigi Buffon in 2013.

Appearing alongside other footballers such as Ronaldo, Eric Cantona, Luís Figo, Patrick Kluivert, and Jorge Campos, they defend "the beautiful game" against a team of demonic warriors.