Editing Paolo Maldini (section)

==Club career==
===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 Primavera|AC Milan youth academy]]. Before that, he had only played [[Street football (association football)|street football]]. He successfully played the test game as a [[Midfielder#Wide midfielder|right midfielder or winger]] in the 4–4–2 formation and was accepted into his age group's squad.<ref>{{cite web | url=https://www.milannews.it/news/maldini-vi-racconto-il-mio-provino-con-il-milan-se-non-fosse-arrivato-berlusconi-e-le-ambizioni-di-vittoria-potevo-andare-altrove-534739 | title=Maldini: "Vi racconto il mio provino con il Milan. Se non fosse arrivato Berlusconi e le ambizioni di vittoria potevo andare altrove" }}</ref> He would continue playing in this position until the age of 14, when he was moved to right [[Association football positions#Full-back|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.<ref>{{cite web | url=https://www.milannews.it/gli-ex/maldini-nelle-giovanili-giocavo-a-destra-mi-piaceva-fare-l-ala-e-dribblare-534751 | title=Maldini: "Nelle giovanili giocavo a destra. Mi piaceva fare l'ala e dribblare..." | access-date=12 May 2024 | archive-date=12 May 2024 | archive-url=https://web.archive.org/web/20240512195027/https://www.milannews.it/gli-ex/maldini-nelle-giovanili-giocavo-a-destra-mi-piaceva-fare-l-ala-e-dribblare-534751 | url-status=live }}</ref>

Maldini won the [[Coppa Italia Primavera]] with the Milan Youth side during the [[1984–85 Serie A|1984–85 season]], and he made his [[Serie A|league]] debut for Milan under manager [[Nils Liedholm]] during the [[1984–85 Serie A|same season]] on 20 January 1985, replacing the injured [[Sergio Battistini]] in a match against [[Udinese Calcio|Udinese]] at age 16.<ref>{{cite news | url=http://blogs.guardian.co.uk/sport/2007/05/23/maldini_the_fulcrum_of_milan_g.html | title=Maldini the fulcrum of Milan generation game | access-date=28 May 2007 | work=Guardian | location=London | first=Richard | last=Williams | date=23 May 2007 | archive-date=25 May 2007 | archive-url=https://web.archive.org/web/20070525131550/http://blogs.guardian.co.uk/sport/2007/05/23/maldini_the_fulcrum_of_milan_g.html | url-status=live }}</ref> It was his only league appearance of the campaign, but he was immediately made a member of the starting eleven the [[1985–86 Serie A|following season]], at age 17, at right-back, being handed the number 3 shirt, which had previously also belonged to his father, Cesare.<ref>{{cite web|url=http://www.gazzetta.it/Calcio/storie/12-08-2017/88-buffon-44gatti-1-ardiles-storia-numeri-pazzi/3-famiglia-maldini.shtml|title=L'88 di Buffon, il "44Gatti" e l'1 di Ardiles: storia dei numeri pazzi|work=La Gazzetta dello Sport|language=it|first=Martina|last=Mazzaro|date=13 August 2017|access-date=23 August 2017|archive-date=24 August 2017|archive-url=https://web.archive.org/web/20170824051746/http://www.gazzetta.it/Calcio/storie/12-08-2017/88-buffon-44gatti-1-ardiles-storia-numeri-pazzi/3-famiglia-maldini.shtml|url-status=live}}</ref> 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.<ref name="Date – Paolo Maldini"/> He scored the first of his 29 goals in [[Serie A]] on 4 January 1987<ref>{{cite web|url=http://www.acmilan.com/it/news/show/85323|title=Dove c'è un abbraccio ...|publisher=AC Milan|language=it|access-date=24 July 2014|archive-date=6 March 2013|archive-url=https://archive.today/20130306142444/http://www.acmilan.com/it/news/show/85323|url-status=live}}</ref> in a 1–0 win against [[Calcio Como|Como]].<ref name="paolo">{{cite web |url=http://www.magliarossonera.it/protagonisti/Gioc-Maldinip.html |title=Paolo Cesare Maldini |publisher=MagliaRossonera.it |language=it |access-date=19 June 2010 |archive-date=15 October 2018 |archive-url=https://web.archive.org/web/20181015172900/http://www.magliarossonera.it/protagonisti/Gioc-Maldinip.html |url-status=live }}</ref><ref name="Paolo MaIdini: Io sono leggenda">{{cite web|url=http://www.storiedicalcio.altervista.org/paolo_maldini.html|title=Paolo MaIdini: Io sono leggenda|publisher=Storie di Calcio|language=it|access-date=30 May 2015|archive-date=24 September 2015|archive-url=https://web.archive.org/web/20150924123046/http://www.storiedicalcio.altervista.org/paolo_maldini.html|url-status=live}}</ref>

===1987–1991: Domestic and international success with ''The immortals''===
The [[1987–88 Serie A|1987–88]] ''[[Scudetto]]'' under [[Arrigo Sacchi]] marked Maldini's first trophy, and the first of seven league titles, with the club.<ref>{{cite web | url=http://www.uefa.com/competitions/ucl/players/player=428/index.html | title=Paolo Maldini | work=UEFA | access-date=28 May 2007 | archive-date=27 May 2007 | archive-url=https://web.archive.org/web/20070527062801/http://www.uefa.com/competitions/UCL/players/player=428/index.html | url-status=dead }}</ref> 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.<ref name="Belgrade">{{cite news|url=https://www.bbc.com/sport/football/24573761|title=How the Belgrade fog saved the great AC Milan team of 1988-89|work=BBC Sport|first=Tom|last=Rostance|date=5 November 2013|access-date=29 July 2016|archive-date=16 September 2016|archive-url=https://web.archive.org/web/20160916144306/http://www.bbc.com/sport/football/24573761|url-status=live}}</ref> 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.{{efn|See<ref>{{cite web|url=http://www.espnfc.com/club/juventus/111/blog/post/2834534/gianluigi-buffon-record-cements-his-legacy-greatest-keeper|title=Gianluigi Buffon record cements his legacy as greatest keeper of all-time|publisher=ESPN FC|first=James|last=Horncastle|access-date=21 March 2016|date=21 March 2016|archive-date=23 July 2019|archive-url=https://web.archive.org/web/20190723040450/http://www.espnfc.com/club/juventus/111/blog/post/2834534/gianluigi-buffon-record-cements-his-legacy-greatest-keeper|url-status=live}}</ref><ref>{{cite web|url=https://www.theguardian.com/football/blog/2016/mar/21/gianluigi-buffon-clean-sheet-record-juventus-torino-sebastiano-rossi|title=Gianluigi Buffon humble as clean sheet record tumbles, but delight not universal|work=The Guardian|first=Nicky|last=Bandini|date=21 March 2016|access-date=21 March 2016|archive-date=26 July 2019|archive-url=https://web.archive.org/web/20190726183438/https://www.theguardian.com/football/blog/2016/mar/21/gianluigi-buffon-clean-sheet-record-juventus-torino-sebastiano-rossi|url-status=live}}</ref><ref>{{cite web|url=https://www.theguardian.com/football/blog/2009/may/08/joy-of-six-great-defences|title=The Joy of Six: Great defences|work=The Guardian|first=Rob|last=Smyth|date=8 May 2009|access-date=9 March 2016|archive-date=16 February 2021|archive-url=https://web.archive.org/web/20210216083337/https://www.theguardian.com/football/blog/2009/may/08/joy-of-six-great-defences|url-status=live}}</ref><ref>{{cite web|url=http://www.repubblica.it/sport/calcio/nazionale/2013/11/19/news/rivoluzione_filosofica_prandelli-71352856/?refresh_ce|title=Nazionale: 2013, addio al catenaccio. Balotelli-Rossi coppia mondiale|work=La Repubblica|language=it|date=19 November 2013|access-date=9 March 2016|archive-date=8 October 2021|archive-url=https://web.archive.org/web/20211008115617/https://www.repubblica.it/sport/calcio/nazionale/2013/11/19/news/rivoluzione_filosofica_prandelli-71352856/?refresh_ce|url-status=live}}</ref><ref>{{cite book|last1=Foot|first1=John|title=Winning at All Costs: A Scandalous History of Italian Soccer|date=2006|publisher=Nation Books|location=New York|page=228}}</ref><ref>{{cite web|url=http://it.eurosport.com/calcio/la-storia-della-tattica-da-sacchi-a-guardiola_sto4735853/story.shtml|title=La storia della tattica: da Sacchi a Guardiola|publisher=Eurosport|language=it|first=Mattia|last=Fontana|date=19 August 2014|access-date=10 March 2016}}</ref><ref>{{cite web|url=http://www.storiedicalcio.altervista.org/milan_sacchi_capello.html|title=MILAN 1988-1994: 6 ANNI DA CAMPIONI|publisher=Storie di Calcio|language=it|first=Corrado|last=Sannucci|date=28 November 2015|access-date=10 March 2016|archive-date=6 October 2016|archive-url=https://web.archive.org/web/20161006053937/http://www.storiedicalcio.altervista.org/milan_sacchi_capello.html|url-status=live}}</ref><ref>{{cite web|url=http://www.calciomercato.it/news/162238/VIDEO---Speciale-squadre-nella-leggenda-Milan-93-94-vs-Inter-09-10.html|title=Speciale squadre nella leggenda, Milan '93-'94 vs Inter '09-'10|publisher=Calciomercato.it|language=it|first=Jonathan|last=Terreni|date=19 June 2012|access-date=10 March 2016|archive-date=10 March 2016|archive-url=https://web.archive.org/web/20160310140544/http://www.calciomercato.it/news/162238/VIDEO---Speciale-squadre-nella-leggenda-Milan-93-94-vs-Inter-09-10.html|url-status=dead}}</ref>}} 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 European Cup|1988–89]] and [[1989–90 European Cup|1989–90]], while Milan finished in third and in second place in Serie A during those respective seasons.<ref name="paolo"/><ref name="Paolo MaIdini: Io sono leggenda"/> On 19 February 1989, Maldini made his 100th appearance in Serie A.<ref name="Date – Paolo Maldini"/>

Milan reached the final of the [[1989–90 Coppa Italia]], losing out to [[Juventus FC|Juventus]]. Milan also managed to capture successive [[European Super Cup]] titles in [[1989 European Super Cup|1989]] and [[1990 European Super Cup|1990]], as well as successive [[Intercontinental Cup (1960–2004)|Intercontinental Cup]] titles, once again [[1989 Intercontinental Cup|1989]] and [[1990 Intercontinental Cup|1990]]. The following season, in Sacchi's final season with the club, Milan were eliminated in the quarter-finals of the [[1990–91 European Cup|European Cup]] by eventual finalists [[Olympique de Marseille|Marseille]], and finished second in [[1990–91 Serie A|Serie A]], behind [[U.C. Sampdoria|Sampdoria]], once again with the best defence in the league, conceding only 19 goals. Milan reached the semi-finals of the [[1990–91 Coppa Italia|Coppa Italia]], losing out to eventual champions [[AS Roma|Roma]]. In 1989, Maldini was awarded the [[Bravo Award]], as the best under-23 player in [[UEFA club competitions|European Competitions]].<ref name="paolo"/><ref name="Paolo MaIdini: Io sono leggenda"/>

===1991–1996: Continued success with ''The invincibles''===
Under Sacchi's replacement, Fabio Capello, Milan continued to be a dominant force in Italy and in Europe. Maldini was also part of Milan's undefeated Serie A team, which won the championship in the [[1991–92 Serie A|1991–92 season]]; in total, Milan went unbeaten for an Italian record of 58 league matches, earning the nickname "The Invincibles".<ref name=ubeaten>{{cite web|url=http://www.uefa.com/memberassociations/news/newsid=1745954.html|title=The longest unbeaten runs in European football|publisher=UEFA|date=4 February 2016|access-date=29 July 2016|archive-date=14 June 2017|archive-url=https://web.archive.org/web/20170614055608/http://www.uefa.com/memberassociations/news/newsid=1745954.html|url-status=dead}}</ref> This championship was Milan's first of three consecutive Serie A titles under Capello in the early 1990s. Maldini helped Milan defend the [[1992–93 Serie A|Serie A title]] the following season, and reach the first of three consecutive [[List of European Cup and UEFA Champions League finals|UEFA Champions League finals]]. Milan lost the [[1993 UEFA Champions League final|1993 Champions League final]] in a 1–0 defeat to Marseille. That season, Maldini scored his first goal in [[UEFA club competitions|European Competitions]] on 21 October 1992 in a 1–0 Champions League win against [[ŠK Slovan Bratislava|Slovan Bratislava]],<ref name="paolo"/> and also made his 200th appearance in Serie A on 4 October of the same year.<ref name="Date – Paolo Maldini"/> The following season, Milan captured their third consecutive [[1993–94 Serie A|Serie A title]], finishing with the best defence in Italy, conceding just 15 goals. Maldini also helped lead Milan to a second consecutive [[1994 UEFA Champions League final|Champions League final]], where he helped his team defeat [[FC Barcelona|Barcelona]]. 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]].<ref name="Dream"/> 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]].<ref name="paolo"/><ref name="Paolo MaIdini: Io sono leggenda"/><ref name="Dream">{{cite news|url=https://www.theguardian.com/sport/blog/2012/mar/28/barcelona-milan-champions-league-1994|title=Barcelona v Milan revisited: The night in 1994 the Dream died|work=The Guardian|first=Sid|last=Lowe|authorlink=Sid Lowe|date=28 March 2012|access-date=10 April 2015|archive-date=7 October 2021|archive-url=https://web.archive.org/web/20211007122050/https://www.theguardian.com/sport/blog/2012/mar/28/barcelona-milan-champions-league-1994|url-status=live}}</ref>

After winning his third Champions League title and reaching the [[1994 FIFA World Cup|1994 World Cup]] final, Maldini became the first defender ever to win ''[[World Soccer Magazine|World Soccer]]'' magazine's annual [[World Soccer Magazine#Award winners|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".<ref name=speech>{{cite web |url=http://www.cs.wm.edu/~wm/maldini.html |title=Paolo Maldini |access-date=25 April 2008 |archive-url=https://web.archive.org/web/20080511045346/http://www.cs.wm.edu/~wm/maldini.html |archive-date=11 May 2008 |url-status=dead |df=dmy }}</ref> He then singled out Milan captain Franco Baresi as a player who "really [deserved] to receive the sort of award I have received".<ref name=speech/> Maldini also placed third in the [[1994 Ballon d'Or]], behind Stoichkov and compatriot [[Roberto Baggio]], and fifth in the [[1994 FIFA World Player of the Year|FIFA World Player of the Year Award]].<ref name="paolo"/><ref name="Paolo MaIdini: Io sono leggenda"/>

The following season, Milan and Maldini captured their third consecutive [[Supercoppa Italiana]] under Capello, and won the [[1994 European Super Cup|European Super Cup]], missing out on the [[1994 Intercontinental Cup|Intercontinental Cup]]. After three consecutive titles, Milan were unable to retain their [[1994–95 Serie A|Serie A title]], although they reached their third consecutive [[1995 UEFA Champions League Final|Champions League final]], where they were defeated 1–0 by [[AFC Ajax|Ajax]]. Maldini came second behind future teammate [[George Weah]] in the [[1995 FIFA World Player of the Year]] Award for his performances. On 17 February 1995, he made his 300th appearance in Serie A.<ref name="Date – Paolo Maldini"/> Maldini was able to capture his fifth Serie A title, and his fourth under Capello, the [[1995–96 Serie A|following season]].<ref name="paolo"/><ref name="Paolo MaIdini: Io sono leggenda"/>

===1996–2001: Assuming the captaincy, struggles, and 1999 Serie A title===
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 [[1996 Supercoppa Italiana|Supercoppa Italiana]] to [[ACF Fiorentina|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 UEFA Champions League|1996–97 Champions League]]. Following Franco Baresi's and Mauro Tassotti's retirement after the [[1996–97 AC Milan season|1996–97 season]], Maldini was appointed Milan's [[Captain (association football)|captain]]. Despite the difficulties Milan encountered during this period, through Maldini's leadership, they reached the [[1998 Coppa Italia final|Coppa Italia final in 1998]], losing to [[SS Lazio|Lazio]], and won the [[1998–99 Serie A|1998–99 Serie A title]] under [[Alberto Zaccheroni]], finishing one point ahead of Lazio. He made his 400th Serie A appearance on 25 April 1999.<ref name="Date – Paolo Maldini"/> In the [[1999–2000 AC Milan season|1999–2000 season]], Milan lost the [[1999 Supercoppa Italiana|Supercoppa Italiana]] against [[Parma Calcio 1913|Parma]], finished third in [[1999–2000 Serie A|Serie A]] and finished bottom of their [[1999–2000 UEFA Champions League group stage|Champions League group]]. Milan were eliminated in the second round of the [[2000–01 UEFA Champions League|Champions League]] the next season and finished in sixth place in [[2000–01 Serie A|Serie A]], failing to qualify for the Champions League, and participated in the [[UEFA Europa League|UEFA Cup]] the following season.<ref name="paolo"/><ref name="Paolo MaIdini: Io sono leggenda"/>

===2001–2007: New era of success===
[[File:A.C. Milan lifting the European Cup after winning the 2002–03 UEFA Champions League - 20030528.jpg|thumb|right|Maldini lifting the European Cup for Milan after winning the [[2003 UEFA Champions League final]]]]

Milan again became a dominant force in Italy and in Europe under [[Carlo Ancelotti]]. In the [[2001–02 Serie A|2001–02 season]], Milan finished in fourth place, qualifying for the Champions League, and also reached their best ever finish in the [[2001–02 UEFA Cup|UEFA Cup]], losing in the semi-finals. In 2002, Maldini was awarded the [[Premio Nazionale Carriera Esemplare "Gaetano Scirea"]], for his career achievements and personality.<ref name="comune.cinisello-balsamo.mi.it">{{cite web|title=Premio Nazionale Carriera Esemplare "Gaetano Scirea": Alba d'Oro|url=http://www.comune.cinisello-balsamo.mi.it/spip.php?article3932|access-date=21 January 2015|archive-date=22 October 2020|archive-url=https://web.archive.org/web/20201022191358/https://www.comune.cinisello-balsamo.mi.it/spip.php?article3932|url-status=live}}</ref> The following season, Maldini lined up with [[Alessandro Nesta]], Alessandro Costacurta and [[Cafu]], who, along with [[Jaap Stam]] during the [[2004–05 AC Milan season|2004–05 season]], formed a formidable defensive lineup in Italy and in Europe. Milan finished third in [[2002–03 Serie A|Serie A]], but Maldini won the first [[2002–03 Coppa Italia|Coppa Italia]] of his career, defeating Roma in the final.<ref name="paolo"/><ref name="Paolo MaIdini: Io sono leggenda"/> On 15 March 2003, he made his 500th appearance in Serie A.<ref name="Date – Paolo Maldini"/>

Milan won the [[2002–03 UEFA Champions League|2002–03 Champions League]] with Maldini as their captain for the first time in his career, in the first all-Italian final, against Juventus, on 28 May 2003 at [[Old Trafford]]. Maldini helped Milan keep a clean sheet, as they defeated Juventus 3–2 on penalties after a 0–0 deadlock following extra time. On that day, it was exactly 40 years since his father, [[Cesare Maldini|Cesare]], had also lifted the [[1963 European Cup final|European Cup trophy]] as Milan's captain, also in England.<ref>{{cite web|url=http://www.uefa.com/memberassociations/association=ita/news/newsid=834649.html|title=Retiring Maldini celebrates the beauty of Milan|publisher=UEFA|date=29 May 2009|access-date=29 January 2016|archive-date=15 February 2020|archive-url=https://web.archive.org/web/20200215212950/https://www.uefa.com/memberassociations/association=ita/news/newsid=834649.html|url-status=dead}}</ref> He and his father are only one of three other father-son pairs to have also done so; the others being [[Manuel Sanchís Martínez|Manuel]] and [[Manolo Sanchís]] of [[Real Madrid C.F.|Real Madrid]], and [[Carles Busquets|Carles]] and [[Sergio Busquets]] of Barcelona. Maldini was elected [[2003 UEFA Champions League final|Man of the Match]] and was named in the [[UEFA Team of the Year]] for the first time in his career.<ref name="paolo"/><ref name="Paolo MaIdini: Io sono leggenda"/>

The following season, Milan were defeated by Juventus on penalties in the [[2003 Supercoppa Italiana|Supercoppa Italiana]], and in the [[2003 Intercontinental Cup|Intercontinental Cup]] final by [[Boca Juniors]], once again on penalties, but managed to defeat [[FC Porto|Porto]] to capture yet another [[2003 UEFA Super Cup|UEFA Super Cup]]. Maldini placed third in the [[2003 Ballon d'Or]] for the second time in his career. Maldini went on to captain Milan to win the [[2003–04 Serie A|Serie A title]] that season, with a record 82 points, whilst Milan were eliminated in the semi-finals of the [[2003–04 Coppa Italia|Coppa Italia]] by Lazio, and in the quarter-finals of the [[2003–04 UEFA Champions League|Champions League]] by [[Deportivo de La Coruña]]. In April 2004, Maldini placed tenth on the ''[[UEFA Golden Jubilee Poll]]'', an online [[UEFA]] survey, which was organised to commemorate the best European footballers of the past 50 years. Maldini was the second-highest placed Italian after [[Dino Zoff]].<ref name="uefa.com">{{cite web|url=https://www.uefa.com/newsfiles/171606.pdf|title=Zinedine Zidane voted top player by fans|publisher=UEFA|access-date=24 July 2014|archive-date=24 October 2012|archive-url=https://web.archive.org/web/20121024165721/http://www.uefa.com/newsfiles/171606.pdf|url-status=live}}</ref> Maldini was also included in the [[FIFA 100|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 [[Oscar del Calcio|Italian footballing Awards]].<ref name="paolo"/><ref name="Paolo MaIdini: Io sono leggenda"/>

[[File:AC Milan team celebrate.jpg|thumb|left|Maldini celebrating the [[2007 UEFA Champions League final|2007 UEFA Champions League]] triumph with his Milan teammates. At 38, he was the oldest captain to lift the trophy.]]

Maldini began the next season by lifting the [[2004 Supercoppa Italiana]] as captain after Milan defeated Lazio. Milan finished second in [[2004–05 Serie A|Serie A]] to Juventus that season, and reached the [[2005 UEFA Champions League final|Champions League final]], only to lose out on penalties to [[Liverpool F.C.|Liverpool]], although Maldini opened the scoring in the first minute. In 2005, Maldini was elected to be a part of the [[UEFA Team of the Year]] for the second time in his career, and was also elected to be the part of the [[FIFPro World XI]] for the first time in his career. The following season, Milan finished second behind Juventus in [[2005–06 Serie A|Serie A]] once again, and reached the [[2005–06 UEFA Champions League|Champions League semi-finals]], only to be defeated by [[2006 UEFA Champions League final|eventual champions]] Barcelona. Both Juventus and Milan were later deducted points for being involved in the [[2006 Italian football scandal|2006 "''Calciopoli''" matchfixing scandal]], and the title was awarded to [[Inter Milan|Internazionale]], while Juventus were relegated, with Milan finishing in third place after the point deduction. During the season, Maldini scored his first and only double of his career, against [[Reggina Calcio|Reggina]]. On 25 September 2005, Maldini broke Dino Zoff's Serie A appearance record after playing his 571st league match against [[Treviso F.B.C.|Treviso]];<ref>{{cite web|url=http://soccernet.espn.go.com/news/story?id=343889&&cc=3888|title=Maldini sets record|date=25 September 2005|website=[[ESPN]]|url-status=dead|archive-url=https://archive.today/20120714110456/http://soccernet.espn.go.com/news/story?id=343889&&cc=5739|archive-date=14 July 2012|access-date=25 April 2008}}</ref> seven days earlier, he had played his 800th game in all competitions for Milan.<ref name="paolo"/><ref name="Paolo MaIdini: Io sono leggenda"/>

The following season, Maldini helped to captain Milan to a [[2006–07 Serie A|fourth-place finish]], despite their point deduction, leading them to obtain a crucial Champions League qualifying spot. Maldini played his 600th Serie A match on 13 May 2007 in a 1–1 draw at [[Calcio Catania|Catania]].<ref>{{cite web | url=http://www.gazzetta.it/Calcio/SerieA/Squadre/Milan/Primo_Piano/2007/05_Maggio/14/MALDINI.shtml | title=Maldini infinito: e sono 600 | publisher=[[Gazzetta dello Sport]] | access-date=14 May 2007 | date=14 May 2007 | language=it | archive-date=25 July 2013 | archive-url=https://web.archive.org/web/20130725154132/http://www.gazzetta.it/Calcio/SerieA/Squadre/Milan/Primo_Piano/2007/05_Maggio/14/MALDINI.shtml | url-status=live }}</ref> 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 [[2007 UEFA Champions League final|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.<ref>{{cite web|title=Oldest person to captain a European Cup / Champions League-winning team: Paolo Maldini|date=23 May 2007|url=http://www.guinnessworldrecords.com/records-5000/oldest-person-to-captain-a-european-cup-champions-league-winning-team/|access-date=23 July 2014|archive-date=26 July 2014|archive-url=https://web.archive.org/web/20140726230245/http://www.guinnessworldrecords.com/records-5000/oldest-person-to-captain-a-european-cup-champions-league-winning-team/|url-status=live}}</ref> 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 Football Awards|UEFA Club Defender of the Year]] for his 2007 performances.<ref name="paolo"/><ref name="Paolo MaIdini: Io sono leggenda"/>

In 2007, after Milan won the [[2007 UEFA Super Cup|UEFA Super Cup]] against [[Sevilla FC|Sevilla]] (although Maldini did not appear in the match), Maldini became the first European captain to lift the [[FIFA Club World Cup 2007|FIFA Club World Cup]] after defeating Boca Juniors on 16 December. He announced his plans to retire at the end of the [[2007–08 Serie A|2007–08 season]], saying that he would do so with "no regrets".<ref>{{cite news | url=http://news.bbc.co.uk/sport1/hi/football/europe/7146949.stm | title=Maldini to quit at end of season | work=BBC Sport | access-date=17 December 2007 | date=16 December 2007 | archive-date=18 December 2007 | archive-url=https://web.archive.org/web/20071218083916/http://news.bbc.co.uk/sport1/hi/football/europe/7146949.stm | url-status=live }}</ref> Following Milan's elimination from the Champions League by [[Arsenal F.C.|Arsenal]] in March, however, Maldini stated that he would possibly delay his retirement for at least a further year.<ref>{{cite web | url=http://fourfourtwo.com/news/italy/7633/default.aspx | title=Injured Maldini's career could be over | access-date=16 April 2008 | work=FourFourTwo | url-status=dead | archive-url=https://web.archive.org/web/20120327102702/http://fourfourtwo.com/news/italy/7633/default.aspx | archive-date=27 March 2012 | df=dmy-all }}</ref> He signed an extension on 6 June that kept him at Milan for the [[2008–09 AC Milan season|2008–09 season]].<ref>{{cite news|url=http://news.bbc.co.uk/sport1/hi/football/europe/7441109.stm|title=Maldini to play for one more year|date=6 June 2008|publisher=BBC|access-date=3 January 2009|archive-date=23 December 2020|archive-url=https://web.archive.org/web/20201223170300/http://news.bbc.co.uk/sport2/hi/football/europe/7441109.stm|url-status=live}}</ref>

===2008–2009: Final years and retirement===
[[File:PaoloMaldini.jpg|thumb|Maldini playing for Milan in 2008|upright=0.8]]
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,<ref>{{cite web | url = http://www.gazzetta.it/Calcio/Primo_Piano/2008/02_Febbraio/16/ParmaMilan.shtml | title = Anche il Parma frena il Milan | work = [[La Gazzetta dello Sport]] | language = it | date = 16 February 2008 | access-date = 25 April 2008 | archive-date = 13 January 2009 | archive-url = https://web.archive.org/web/20090113043518/http://www.gazzetta.it/Calcio/Primo_Piano/2008/02_Febbraio/16/ParmaMilan.shtml | url-status = live }}</ref><ref>{{cite web|url=http://www.acmilan.com/it/news/show/61968|title=1000 Maldini|publisher=AC Milan|access-date=24 July 2014|archive-date=13 May 2011|archive-url=https://web.archive.org/web/20110513230320/http://www.acmilan.com/it/news/show/61968|url-status=live}}</ref> of which 861 were with Milan, 12 with the [[Italy national under-21 football team|Italy under-21 side]], 1 with the Italian Olympic team and 126 with the [[Italy national football team|Italy senior team]].<ref>{{cite web|url=http://it.archive.uefa.com/competitions/ucl/news/kind=1/newsid=659489.html|title=Maldini mille e una notte|website=[[UEFA]]|access-date=24 July 2014|url-status=dead|archive-url=https://archive.today/20120720194532/http://it.archive.uefa.com/competitions/ucl/news/kind=1/newsid=659489.html|archive-date=20 July 2012|df=dmy-all}}</ref> 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 UEFA Champions League|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.<ref name="Paolo MaIdini: Io sono leggenda"/><ref name="gazzetta.it">{{cite web|url=http://www.gazzetta.it/Calcio/Primo_Piano/2008/10/27/Maldini.shtml|title=Maldini come Facchetti "Stile, carisma e fedeltà|work=La Gazzetta dello Sport|language=it|date=27 October 2008|access-date=20 January 2015|archive-date=4 March 2016|archive-url=https://web.archive.org/web/20160304100234/http://www.gazzetta.it/Calcio/Primo_Piano/2008/10/27/Maldini.shtml|url-status=live}}</ref>

On 18 April 2009, Maldini announced that he would retire at the end of the 2008–09 season.<ref name="paolo"/><ref name="Paolo MaIdini: Io sono leggenda"/> On 17 May 2009, in the [[Stadio Friuli]], Maldini played his 900th official match for Milan in a league game against Udinese. Maldini's last match in San Siro was on 24 May, a 3–2 loss against Roma, and was given a standing ovation by the fans. There was a small controversy, however, when the Milan Ultras fans known as ''Brigate Rossonere'' protested against Maldini as he said goodbye.<ref>{{cite web | url = http://www.goal.com/en/news/10/italy/2009/05/25/1285122/why-did-milan-ultras-insult-paolo-maldini | title = Why Did Milan Ultras Insult Paolo Maldini? | publisher = goal.com | date = 25 May 2009 | access-date = 16 April 2011 | archive-date = 14 April 2010 | archive-url = https://web.archive.org/web/20100414011110/http://www.goal.com/en/news/10/italy/2009/05/25/1285122/why-did-milan-ultras-insult-paolo-maldini | url-status = live }}</ref><ref>{{cite news|last=Marcotti|first=Gabriele|url=https://www.thetimes.com/travel/destinations/europe-travel/italy/paolo-maldini-farewell-not-so-fond-from-ac-milan-hard-core-m2hzxbnbpqf|title=Paolo Maldini farewell not so fond from A.C. Milan hard core|date=25 May 2009|work=[[The Times]]|location=London|access-date=23 March 2020|archive-date=23 March 2020|archive-url=https://web.archive.org/web/20200323221907/https://www.thetimes.co.uk/article/paolo-maldini-farewell-not-so-fond-from-ac-milan-hard-core-m2hzxbnbpqf|url-status=live}}</ref> 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 numbers in association football|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.<ref name="Paolo MaIdini: Io sono leggenda"/><ref>{{cite web | url=https://www.fifa.com/worldfootball/news/newsid=96207.html | archive-url=https://web.archive.org/web/20071211160318/http://www.fifa.com/worldfootball/news/newsid=96207.html | url-status=dead | archive-date=11 December 2007 | title=Paolo Maldini: like father, like son | access-date=30 November 2011 | work=FIFA}}</ref><ref>{{cite news | url=https://www.thestar.com/article/184399/ | title=The monarch of defence | access-date=6 May 2005 | work=Toronto Star | first=Cathal | last=Kelly | archive-date=14 May 2007 | archive-url=https://web.archive.org/web/20070514061523/http://www.thestar.com/article/184399 | url-status=live }}</ref>

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 UEFA Champions League|2009–10 Champions League]].<ref>{{cite web|url=http://www.lastampa.it/multimedia/multimedia.asp?IDmsezione=11&IDalbum=20175&tipo=FOTOGALLERY|title=Uefa, premio alla carriera per Paolo Maldini|work=La Stampa|language=it|access-date=24 July 2014|archive-date=13 April 2014|archive-url=https://web.archive.org/web/20140413185647/http://www1.lastampa.it/multimedia/multimedia.asp?IDmsezione=11&IDalbum=20175&tipo=FOTOGALLERY|url-status=dead}}</ref> On 17 November 2009, Spanish sports newspaper ''[[Marca (newspaper)|Marca]]'' awarded Maldini the "Marca Leyenda" prize for his career and achievements.<ref name=marca.com>{{cite web|url=http://www.marca.com/2009/11/17/futbol/futbol_internacional/1258450874.html|title=Maldini recibe el MARCA Leyenda|trans-title=Maldini receives the MARCA Leyenda Award|work=Marca|language=es|access-date=24 July 2014|archive-date=12 November 2019|archive-url=https://web.archive.org/web/20191112234326/https://www.marca.com/2009/11/17/futbol/futbol_internacional/1258450874.html|url-status=live}}</ref><ref>{{cite web|url=http://sport.repubblica.it/news/sport/calcio-milan-a-paolo-maldini-premio-marca-leyenda-a-carriera/3734757|title=Calcio, Milan: a Paolo Maldini premio 'Marca Leyenda' alla carriera|work=La Repubblica|language=it|access-date=24 July 2014|archive-date=13 April 2014|archive-url=https://web.archive.org/web/20140413201826/http://sport.repubblica.it/news/sport/calcio-milan-a-paolo-maldini-premio-marca-leyenda-a-carriera/3734757|url-status=live}}</ref>