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In August 2019, Pirlo enrolled in the UEFA Pro Licence courses at Coverciano.

After struggling with persisting physical problems for most of the 2017 MLS season, on 8 October 2017, Pirlo announced that he would retire from professional football at the end of the season; in total, he was limited to only 15 appearances and two assists during the 2017 MLS regular season. He made his final professional appearance on 5 November, coming on as a 90th-minute substitute in a 2–0 home win over Columbus Crew, in the second leg of the 2017 MLS Cup Eastern Conference Semi-finals; New York were eliminated from the Playoffs following a 4–3 aggregate loss. In total, Pirlo made 62 appearances for New York – 60 of which came in the MLS regular season, with the other two coming in the MLS Cup Playoffs – over the course of his three seasons with the club, scoring one goal and providing 18 assists, all of which came during the MLS regular season. Pirlo officially communicated his retirement from professional football the following day, on Twitter. A testimonial match – La Notte del Maestro – was played at the San Siro Stadium in Milan on 21 May 2018, in honour of Pirlo's retirement from professional football.

On 7 July 2017, Pirlo's partner, Valentina Baldini, gave birth to their twins named Leonardo and Tommaso.

Pirlo made his first assist of the 2016 MLS season on 30 April, as he set up a goal for David Villa from a corner in a 3–2 home win over the Vancouver Whitecaps. On 18 June, he scored his first MLS goal from a free kick in the 50th minute of a 3–2 home victory over Philadelphia. In July 2016, Pirlo was included in the roster for the 2016 MLS All-Star Game. Pirlo finished his second MLS season with the club with one goal and a team seasonal best of eleven assists in 32 appearances, as New York City finished in second place in the Eastern Conference, and qualified for the MLS Cup Playoffs for the first time ever, clinching a spot in the Eastern Conference semi-final. He was ruled out of the first leg, however, after sustaining a last-minute calf injury, and New York lost the match 2–0 away to Toronto FC. He appeared in the second leg on 6 November, as New York were eliminated from the Playoffs 7–0 on aggregate, following a 5–0 home defeat to Toronto.

Despite previously announcing his international retirement following the 2014 World Cup, Pirlo reversed his decision, and under new Italy manager, and Pirlo's former Juventus manager Conte, Pirlo returned to the Italian squad. On 10 October, Pirlo started in Italy's second Euro 2016 qualifying match, which ended in a 2–1 home win over Azerbaijan, overtaking Zoff with his 113th appearance for Italy. Pirlo assisted Chiellini's first goal of the match from a corner kick. In August 2015, Pirlo was called for Italy's Euro 2016 qualifying matches against Malta and Bulgaria in September; he appeared in Italy's 1–0 home victory over Malta on 3 September, becoming the first MLS player to represent Italy; this was his final international appearance. In total, Pirlo made four appearances under Conte, as Italy qualified for Euro 2016 on 10 October in a 3–1 win over Azerbaijan. On 23 May 2016, Pirlo, along with fellow MLS compatriot Giovinco, was left off of Conte's 30-player shortlist for Italy's Euro 2016 squad. Regarding their omission, Conte commented in a press conference: "When you make a certain choice and go to play in certain leagues, you do so taking it into account that they could pay the consequences from a footballing viewpoint". In response to Conte's comments, Pirlo stated to Sky Italia: "I have spoken to Conte and there is no disappointment on my part, he knows what he has to do and what he should not do. We had discussions during the season and both parties made their own decisions. He is the coach and it's only right he makes his decisions and decides what is best for him. I hope Italy win although the favourites are other teams such as Germany, Spain and France."

In July 2016, it was reported that Pirlo's jersey was the highest-selling MLS shirt in 2016.

On 6 July 2015, it was announced that Pirlo had completed a move to Major League Soccer (MLS) expansion franchise New York City as their third Designated Player. In doing so, he became the highest paid Italian player in all leagues with an $8 million salary, until Graziano Pellè overtook him after moving to Chinese club Shandong Luneng the following year. Pirlo made his debut with the club on 26 July 2015 at Yankee Stadium in New York against Orlando City, coming on as a substitute in the 56th minute; he was involved in his team's third and fourth goals and was booked in the 88th minute as New York won the match 5–3. He made his first start for New York on 1 August, in a 2–3 home defeat to the Montreal Impact. On 12 August, it was announced that Pirlo had placed seventh in the 2015 UEFA Best Player in Europe. On 13 August he set up a goal for David Villa in a 3–1 home win over D.C. United. In October 2015, Pirlo was named to the 59-player shortlist for the 2015 FIFA Ballon d'Or. He finished the 2015 MLS season with 5 assists in 13 appearances, and ended up third in the MLS in minutes per pass, although he failed to score a goal. Despite the presence of Pirlo and two other UEFA Champions League winners, David Villa and Frank Lampard, New York City failed to qualify for the 2015 MLS Cup Playoffs at the conclusion of their debut season, which drew criticism from the press; Pirlo in particular drew criticism from the media for his low defensive work-rate. In November, Pirlo became the first MLS player in history to be nominated for the FIFPro World XI.

On 11 June 2014, Pirlo signed a new contract keeping him at Juventus until 2016. Pirlo made his 100th league appearance for Juventus in a 3–2 home win over Roma on 5 October 2014. On 1 November, Pirlo scored Juventus's opening goal from a free kick in a 2–0 win over Empoli, on their 117th anniversary; this was his 26th goal from a free kick in Serie A, putting him two goals behind the all-time record holder, Siniša Mihajlović. On 4 November, Pirlo scored once again from a trademark, curling direct free kick in a 3–2 home win over Olympiacos in a group-stage UEFA Champions League fixture. This was Pirlo's 100th appearance in the UEFA Champions League, marking the occasion with his first UEFA Champions League goal with Juventus. On 15 December 2014, Pirlo was named the Serie A Footballer of the Year for the third time in his career, and for the third consecutive year since his arrival at Juventus; he was also named part of the 2014 Serie A Team of the Year. In Juventus's 2–1 home victory over Borussia Dortmund in the round of 16 of the UEFA Champions League, on 24 February 2015, Pirlo left the pitch during the first half of the match, after injuring his right calf, ruling him out for three weeks. Pirlo was called up on 11 April 2015 against Parma following his injury. He returned to the starting line-up on 14 April 2015, helping Álvaro Morata to win a penalty which was later converted by Vidal in a 1–0 victory over Monaco at the Juventus Stadium, in the first leg of the UEFA Champions League quarter-finals; he was replaced by Andrea Barzagli during the second half. On 26 April, Pirlo scored from a free kick in a 2–1 away defeat to local rivals Torino in the "Derby di Torino"; this was his 28th goal in Serie A from a free kick, which put him level with Mihajlović as the player with the most goals from free kicks in Serie A history. On 20 May, Pirlo played a part in both of Juventus's goals as the Turin club defeated Lazio 2–1 at the Stadio Olimpico in the 2015 Coppa Italia Final. On 6 June 2015, Pirlo played the entirety of the 2015 UEFA Champions League Final as Juventus were defeated 3–1 by Barcelona at Berlin's Olympiastadion; this was the final game of his Juventus career. Pirlo was named to the 2014–15 UEFA Champions League Squad of the season for his performances.

In the 2014 World Cup, Italy were placed in Group D, along with Costa Rica, England and Uruguay, in what was called the "Group of Death". On 14 June, in Italy's opening match against England, Pirlo wore the captain's armband due to Buffon's last minute injury. The match ended with a 2–1 win to Italy. Pirlo heavily contributed to Italy's win, controlling the flow of the game, and setting up several goalscoring chances, as Italy dominated possession. During the match, Pirlo made 108 passes in total, only misplacing five, with a pass completion rate of 95.4%, completing the most passes of any other player in the previous opening matches of the 2014 World Cup. With a 93.2 pass percentage, Italy also managed to record the highest pass accuracy percentage of any team in a World Cup match since Denmark in the 1966 World Cup, completing 561 of their 602 passes. Pirlo also contributed to Italy's first goal of the match: Antonio Candreva's short corner was played to Marco Verratti, who then passed the ball out wide towards Pirlo, who drew his marker with him. Pirlo let the ball pass in between his legs to Marchisio, leaving him with space to score with a low drive from outside the area. Pirlo also managed to hit the crossbar from a swerving free kick in injury time. Italy suffered 1–0 defeats in both of their remaining matches against Costa Rica and Uruguay, however and were eliminated in the group stage for the second consecutive World Cup, finishing in a disappointing third place in their group, behind Costa Rica and Uruguay. Pirlo's appearance against Uruguay was his 112th cap for Italy, which allowed him to equal Dino Zoff's number of appearances for the Italian national team, and made him the fourth most capped player for the Italian national team. The Italian squad and manager, Cesare Prandelli, were criticised for over-relying on Pirlo to create goalscoring chances. Although Pirlo was able to set up some goal scoring opportunities and did test the opposition goalkeepers with some dangerous free kicks in the final two group games, his performances were stifled by the defensive pressure of the opposition, and he was much less dominant than he had been in the opening match against England. Although he had previously communicated his intention to retire after the World Cup, he stated, upon his return to Italy, that he would still be available to play for the national team.

In 2013, Pirlo wrote an autobiography, with Alessandro Alciato, titled Penso Quindi Gioco (I Think Therefore I Play). On 1 September 2014, Pirlo, along with many current and former footballing stars, took part in the "Match for Peace", which was played at the Stadio Olimpico, in Rome, with the proceeds being donated entirely to charity. That same year, he revealed that he supported Inter in his youth, and that his favourite footballers and major influences as a player were German former midfielder Lothar Matthäus – as he played for Inter – and compatriot Roberto Baggio – due to his playing style and role on the pitch as an offensive playmaker, with which Pirlo identified at the time.

It was at A.C. Milan, in particular under manager Carlo Ancelotti, where Pirlo made big strides in developing into a world class player, and one of the best deep-lying playmakers and set-piece specialists in the world, as he went on to achieve notable domestic and international success during his time with the club. Pirlo later recalled the period he has spent in Milan with Ancelotti: "He changed my career, putting me in front of the defence. We shared some unforgettable moments. We had a magnificent past together." After Mazzone's pioneering decision to move Pirlo into a deep-seated playmaking role with Brescia during the previous season, Milan managers Fatih Terim and, in particular, Carlo Ancelotti further developed this role for him at Milan. In Ancelotti's 4–3–1–2 and 4–3–2–1 formations, Pirlo was deployed as a deep-lying playmaker in front of the defence, which allowed him to play alongside other talented attacking midfielders, such as Rivaldo, Rui Costa and eventually Kaká, replacing the gap left by Milan legend Demetrio Albertini in the deep midfield playmaking role. He would become an integral part of the Rossoneri's midfield, forming a formidable partnership with Gennaro Gattuso, as well as with Clarence Seedorf and Massimo Ambrosini, who also supported his playmaking role defensively. Pirlo was given the nickname the metronome during his time at the club, for the way in which he set the team's rhythm.

Pirlo featured in Juventus's 4–0 win against Lazio in the 2013 Supercoppa Italiana, on 18 August 2013, at the Stadio Olimpico, in Rome. Pirlo helped to create Paul Pogba's opening goal in the twenty-third minute of play. Pirlo was the only Italian player to be nominated for the 2013 FIFA Ballon d'Or, and was also nominated for the 2013 FIFPro World XI. On 1 December, Pirlo sustained a knee-ligament injury which would keep him off the field for over a month. On 12 January 2014, Pirlo signed a new contract with Juventus, which will keep him at the club until 2016. On 27 January, Pirlo was named Serie A Footballer of the Year for a second consecutive time, and was once again included in the Serie A Team of the Year. Juventus won their 30th league title that season with a record 102 points and 33 victories; this was also their third consecutive title since Pirlo's arrival. Juventus also reached the quarter-finals of the Coppa Italia, losing out to Roma. The Turin club suffered a group stage elimination in the UEFA Champions League, but managed a semi-final finish in the UEFA Europa League, losing out to Benfica, with Pirlo scoring a match winning goal from a free kick in the round of 16 against Fiorentina. Pirlo was chosen to be part of the 2013–14 Europa League Team of the Season, for his performances in the competition.

In the semi-final against Germany on 4 July, he assisted Fabio Grosso's opening goal in the dying minutes of extra-time, and was again named Man of the Match, as Italy triumphed 2–0 over the hosts. In the final against France on 9 July, his corner kick produced Marco Materazzi's equalising header ten minutes after France had opened the scoring with a Zinedine Zidane penalty. Following a 1–1 deadlock after extra-time, the match went to a penalty shoot-out, in which he scored the first spot kick, helping Italy to win the title. Pirlo formed a formidable midfield partnership with Milan teammate Gattuso, and he completed 475 passes out of 580 attempted throughout the tournament, while also winning 18 challenges. After the final, he was named Man of the Match for a third time, winning more Man of the Match Awards than any other player in the tournament. Pirlo was voted the third-best player of the tournament, winning the Bronze Ball, and he finished the victorious World Cup campaign as the top assist provider along with teammate Francesco Totti, as well as Juan Román Riquelme, Bastian Schweinsteiger, and Luís Figo. He was named as part of the 2006 FIFPro XI and as part of the 2006 World Cup Team of the Tournament for his performances, placing ninth in both the 2006 Ballon d'Or and the 2006 FIFA World Player of the Year Awards.

On 24 June, Pirlo produced a Man of the Match performance in the quarter-finals against England, as Italy won 4–2 on penalties after the game had finished 0–0 in extra time. Pirlo scored in the shoot-out with an audacious chipped penalty down the centre of the goal, also known as a Panenka. Following the match Pirlo spoke of his eloquent penalty, stating, "At the moment I saw the goalkeeper making strange movements, so I waited for him to move and hit it like that... It was easier for me to chip it at that stage. Maybe my effort put some pressure on England." Pirlo completed more passes than the entire England midfield, as he managed 131 passes, the most of any player during the match, and the second most in a single match in the history of the European Championship, behind Xavi, with an 87% pass completion rate, as Italy finished the match with 63% ball possession. He also ran 11.58 kilometres throughout the match, covering more distance than any England player.

In the semi-final round, on 28 June, Pirlo once again put up a Man of the Match performance against Germany, starting the play which led to Balotelli's first goal of the match, as Italy won 2–1 to advance to the final of the tournament. Following Italy's success in the semi-finals, Italy were defeated 4–0 against Spain in the final.

Pirlo was selected for Italy's squad to play in Brazil at the 2013 Confederations Cup. He won his 100th cap on 16 June in Italy's opening game against Mexico, opening the scoring with a trademark free kick as Italy won 2–1, and Pirlo was voted Man of the Match. He was only the fifth Italian player to receive 100 caps after Dino Zoff, Paolo Maldini, Gianluigi Buffon, and Fabio Cannavaro. In the second group stage match against Japan on 19 June, Pirlo assisted De Rossi's goal against from a corner, as the match ended 4–3 to Italy. The win allowed Italy to progress to the semi-finals of the competition for the first time. Pirlo did not play in the third group stage match against hosts Brazil, as he had come down with a minor injury at the end of the second match, although he would be available to play for the semi-finals. Italy were defeated 4–2 in the final group stage match on 22 June, which meant that they finished second in group A, and would be playing the winners of group B, tournament favourites Spain, in a rematch of the European Championship Final of the previous year. Italy held Spain to 0–0 draw on 27 June, as the match eventually went to penalties. Pirlo netted his penalty, but Bonucci's miss allowed Spain to advance to the final, as Italy lost the shoot-out 7–6. Pirlo was injured for the third place final, although Italy managed to defeat Uruguay 3–2 on penalties on 30 June, after a 2–2 draw. Pirlo was named to the Team of the Tournament, and was nominated for the Golden Ball award, although he failed to place amongst the top three players of the tournament, as the awards went to Neymar, Iniesta, and Paulinho, respectively.

Following Pirlo's departure from Milan in 2011, Juventus signed him on a free transfer on a contract until 2014. His debut with Juventus was in a friendly match against Sporting CP, which they lost 2–1. His first competitive match with Juventus was the 2011–12 Serie A opening match against Parma at home, in which he tallied two assists, for Stephan Lichtsteiner and Claudio Marchisio – the latter of which was the first ever goal in the Juventus Stadium –, and completed 110 passes in a 4–1 victory. Antonio Conte played him alongside younger midfielders Marchisio and new signing Arturo Vidal in a three-man midfield, which allowed Pirlo to function creatively as a deep-lying playmaker, while Marchisio and Vidal supported him defensively. Pirlo's first goal for Juventus was a free kick against Catania on 18 February 2012 securing a 3–1 victory for Juventus and put the club back at the top of the Serie A table, above his former club Milan. On 18 March, Pirlo scored in a 5–0 demolition of Fiorentina and after the game dedicated the win to Fabrice Muamba, who suffered a cardiac arrest playing for Bolton Wanderers during a match against Tottenham Hotspur the same day.

Pirlo played in the 2012 Supercoppa Italiana in Beijing on 11 August 2012 against Napoli, helping Juventus to a 4–2 win in extra time. He curled in a free kick to seal a 2–0 defeat of Parma on the opening day of the new Serie A season. The goal caused much controversy, as the Parma players protested that it had not gone over the line, and replays proved inconclusive. In the following league match against Udinese on 2 September, Pirlo helped to win a penalty and assisted Sebastian Giovinco's second goal of the match, as Juventus went on to defeat the home team 4–1. On 29 September, Pirlo opened the scoring when he dispatched a trade mark free kick to send Juventus on their way to a 4–1 defeat of Roma. Pirlo was nominated for the 2012 FIFA Ballon d'Or, along with Juventus and Italy teammate Gianluigi Buffon, following their performances throughout the calendar year. Pirlo provided three assists for Juventus during the group stage, helping them to top their group undefeated and advance to the knockout stages for first time since the 2008–09 tournament. Pirlo was also elected the 2012 Serie A Footballer of the Year, as well as the best midfielder of the season, also winning the 2012 Guerin d'Oro. He was named as part of the 2012 Serie A team of the Year for his performances. Pirlo also won the Pallone Azzurro, given to the best player of the year in the Italian National Team, as well as placing fourth in the IFFHS World's Best Playmaker of the Year Award, and seventh in the FIFA Ballon d'Or. Pirlo and Juventus retained their Serie A title that season. Juventus were, however, eliminated by Bayern Munich in the quarter finals of the UEFA Champions League, and in the semi-finals of the Coppa Italia by Lazio; both of these teams were the winners of these respective competitions.

Because of his excellent performances in leading Juventus to win the Serie A title, Italy coach Cesare Prandelli included the playmaker in his 32-man provisional squad for Euro 2012, and subsequently in Italy's final 23-man squad for the tournament. Pirlo provided the cutting ball from which Antonio Di Natale scored the opening goal of Italy's 1–1 draw with World and European champions Spain in the opening round of group play on 10 June 2012. Pirlo then opened the scoring himself from a direct free kick in Italy's second group match against Croatia on 14 June, which also ended in a 1–1 draw; Pirlo was named Man of the Match. In the final group match against Republic of Ireland, Pirlo set up Antonio Cassano's goal from a corner kick to help Italy take a 1–0 lead. Italy eventually won 2–0 and progressed to the knock-out stage of the tournament as runners-up in Group C.

Pirlo won three Man of the Match Awards at Euro 2012, the most awards won by a single player, along with Andrés Iniesta of tournament champions Spain. Pirlo was nominated for the Player of the Tournament Award, which ultimately went to Iniesta, and he was also elected to be part of the Team of the Tournament.

Pirlo scored one goal during Italy's qualification campaign for the 2014 FIFA World Cup, which saw them top their group, undefeated. Pirlo converted a penalty as Italy dispatched Armenia by a score of 3–1 on 12 October 2012, and assisted several goals during the World Cup qualifying campaign. On 5 June 2014, Pirlo was selected by Italy manager Prandelli as part of his 23-man squad for the 2014 World Cup in Brazil. On 12 June, Pirlo announced that he would retire from international football following the tournament.

Pirlo finished the season by winning the 2011–12 Serie A title, after helping Juventus to secure a 2–0 victory over Cagliari. He provided the most assists in the Serie A that season, with 13, and he also found the back of the net three times in the league. Pirlo created over 100 chances and completed 2643 passes that season, with an 87% pass completion rate, completing 500 more passes than any other player in Serie A; the only player in the world to have completed more passes than him that season was Xavi. Due to his performances throughout the season, and his key role in leading Juventus to their first Serie A title in nine years, he was named to the Serie A Team of the Year, along with his Juventus midfielder partner Vidal. Pirlo and Juventus also finished runners up to Napoli in the Coppa Italia final that season. Pirlo's fine form in the 2011–12 season, in which he led Juventus to the league title, the Supercoppa Italiana and Coppa Italia Final, as well as leading Italy to the final of Euro 2012, saw him nominated for the 2012 UEFA Best Player in Europe Award, in which he finished 4th. He was also elected to be part of the 2012 ESM Team of the Year and the 2012 UEFA Team of the Year.

The following season saw Milan dominate the league. Milan played host to Genoa on 25 September 2010, with Pirlo providing a lifted ball over the top of the defence to set striker Zlatan Ibrahimović free to score the solitary goal of the game. On 2 October, Pirlo scored a 40-yard goal against Parma to give Milan their first away win of the 2010–11 season. On 14 May 2011, Pirlo appeared in his last match for Milan, coming on as a half-time substitute for Ambrosini as the club celebrated their Serie A title with a 4–1 victory over Cagliari. Four days later, Pirlo confirmed that he would be leaving Milan at the end of the 2010–11 season, after a mutual decision not to renew his contract. In his last season in Milan, Pirlo appeared in the league just 17 times under manager Massimiliano Allegri, notching just one goal and three assists, winning his second Serie A title with Milan that season, also reaching the round of 16 in the UEFA Champions League, and in the Coppa Italia semi-final.

Pirlo was not able to play the first two games in the 2010 World Cup for Italy due to recent injuries. He came off the bench for Italy late in the match on 24 June against Slovakia. Even with his help in orchestrating a renewed Italian offence, Pirlo could not prevent Italy from being knocked out of the first round.

Coach Prandelli named Pirlo Vice-Captain of the Italian squad, behind captain, Gianluigi Buffon. Pirlo appeared in nine matches as Italy qualified undefeated for the European Championships in Poland and Ukraine, providing several assists, and netting one goal in Italy's 5–0 victory over the Faroe Islands on 7 September 2010.

After Kaká and Ancelotti left Milan in the summer of 2009, Chelsea tested Milan's resolve by bidding $12 million and Claudio Pizarro for Pirlo. The club rejected the offer and Pirlo was said to be contemplating a transfer request. On 5 August, club owner Silvio Berlusconi decided not to sell Pirlo, who said he was overjoyed and wanted to end his career at Milan. On 21 October 2009, Pirlo scored a notable 30-metre goal in Milan's 3–2 win over Real Madrid in the UEFA Champions League; Milan were eventually eliminated in the round of 16. Milan finished the season with a 3rd place in Serie A, and a quarter-final finish in the Coppa Italia under new manager Leonardo.

On 15 June 2009, Pirlo assisted Giuseppe Rossi's second goal in a 3–1 win in Italy's opening match of the Confederations Cup against the United States. Italy subsequently lost the following two group matches against Egypt and Brazil, and were eliminated from the competition in the first round.

Pirlo appeared in all three of Italy's group matches at UEFA Euro 2008. He was named Man of the Match in Italy's second group match, a 1–1 draw against Romania, on 13 June. On 17 June 2008, Pirlo netted a penalty as Italy defeated France 2–0 in the final group match, to send their rivals and World Cup runners-up crashing out of the European Championships in the first round. Italy lost on penalty kicks to eventual winners Spain in the quarterfinals, as Pirlo and Milan teammate Gattuso were suspended for the match.

Pirlo came in third, second, fourth and third twice more in the International Federation of Football History & Statistics World Playmaker of the Year awards in 2006, 2007, 2012, 2013 and 2015, respectively. He placed fourth in the 2012 UEFA Best Player in Europe Award and seventh in the 2015 edition. He placed seventh in the 2007 FIFA World Player, fifth in the 2007 Ballon d'Or and seventh in the 2012 FIFA Ballon d'Or award. He was also named as part of the 2006 FIFPro World XI and the 2012 UEFA Team of the Year. In 2012, 2013 and 2014, Pirlo was also elected as Serie A Footballer of the Year and was also named as part of the Serie A team of the Year. After helping Juventus to the 2015 UEFA Champions League Final, he was named to the squad of the season. In 2012, Pirlo was named the eighth best footballer in the world by The Guardian. In 2013, Bloomberg ranked him the fifth best player in Europe. In 2015, France Football rated him as one of the 10 best footballers in the world who were over the age of 36.

The following season, Milan once again finished in second place behind Juventus in Serie A (before their 30-point deduction due to their involvement in the 2006 Calciopoli scandal), also reaching the semi-finals of the UEFA Champions League, only to be defeated by eventual champions, Barcelona, and the quarter-finals of the Coppa Italia. In 2006, Pirlo placed 9th in the Ballon d'Or, which was won by his Italy teammate Fabio Cannavaro, and was elected to the 2006 FIFPro World XI.

Pirlo led Milan in minutes played for the 2006–07 season with 2,782 across 52 appearances, as he went on to win his second UEFA Champions League title with Milan, also helping his team to a fourth-place finish in Serie A, and another Coppa Italia semi-final. In the second leg of the UEFA Champions League semi-final against Manchester United, Pirlo set up Seedorf's goal, as Milan progressed on to the final. In the 2007 UEFA Champions League Final in Athens, Pirlo assisted Inzaghi's first goal from a free kick, helping Milan to defeat Liverpool 2–1, avenging their 2005 final defeat in Istanbul. During the 2007–08 season, Pirlo won his second UEFA Super Cup with Milan, assisting Milan's second goal in the final, and winning the Man of the Match award; he also contributed to the club's first ever FIFA Club World Cup title in 2007, once again setting-up Milan's second goal in the final. In October 2007, he was nominated for the 2007 Ballon d'Or, the 2007 FIFA World Player of the Year, and the 2007 International Federation of Football History & Statistics (IFFHS) World's Best Playmaker Awards, but they were all won by Milan teammate Kaká, as Pirlo placed 5th in the Ballon d'or, 7th in the FIFA World Player of the Year, and 2nd in the World's Best Playmaker Awards. Despite a strong start, Milan suffered a dip in form during the second half of the season, finishing the league in fifth place, failing to qualify for the UEFA Champions League; Milan also suffered eliminations in the round of 16 of the UEFA Champions League and the Coppa Italia that season. The following season, Milan managed a second-place finish in Serie A, alongside Juventus, and behind local rivals Inter, whilst they were eliminated in the round of 32 of the UEFA Cup, and the round of 16 of the Coppa Italia.

Pirlo was named to Italy's 23-man squad for the 2006 World Cup, and appeared in all of Italy's matches at the tournament, playing 668 minutes in total. In Italy's first match of the tournament on 12 June, Pirlo scored the opening goal against Ghana, and subsequently helped set up a goal for Vincenzo Iaquinta to seal a 2–0 victory, as the midfielder was named Man of the Match. In the second match on 17 June, he set up a diving header for Gilardino from a set piece which proved to be vital in the 1–1 draw against the United States.

"I don't feel pressure ... I don't give a toss about it. I spent the afternoon of Sunday, 9 July 2006 in Berlin sleeping and playing the PlayStation. In the evening, I went out and won the World Cup."

I thought about quitting because, after Istanbul, nothing made sense any more. The 2005 Champions League final simply suffocated me... We’d invented a new disease with multiple symptoms: "Istanbul syndrome". I no longer felt like a player, and that was devastating enough. But even worse, I no longer felt like a man.

Under Trapattoni's replacement, Marcello Lippi, Pirlo became a key member of Italy's starting line-up during their 2006 World Cup Qualifying campaign, and he was eventually called up as a starting member of the Italian squad for the 2006 FIFA World Cup. On 26 March 2005, he assured Italy's participation in the tournament after scoring from two free kicks in a 2–0 win against Scotland in a World Cup Qualifier.

Milan finished as runners up in Serie A to Juventus in the 2004–05 season. In the 2004–05 UEFA Champions League, Pirlo finished as one of the second highest assist providers with four assists, as he helped Milan to reach the final. In the 2005 UEFA Champions League Final against Liverpool, on 25 May, Pirlo assisted Paolo Maldini's opening goal, after 50 seconds, from a free kick, and combined with Kaká before the Brazilian unleashed Hernán Crespo with a long pass for Milan's third goal before halftime. In the second half, however, Liverpool made a three-goal comeback, sending the match into extra time. After a 3–3 deadlock, the match went to penalties, and Milan were defeated by the English team in the shoot-out. Despite Pirlo's performance throughout the competition and in the final, one of the most forgettable incidents of the season was probably his penalty miss during the shoot-out in the final, as his spot kick was saved by Jerzy Dudek. Pirlo would later state in his autobiography that the 2005 UEFA Champions League Final defeat on penalties was the worst moment of his career, and that he had considered retiring prematurely following the match:

In total with Milan, Pirlo made 401 appearances, scoring 41 goals. With the club, he won two Serie A titles in 2004 and 2011, as well as two UEFA Champions League titles in 2003 and 2007, also reaching the final in 2005; he also won a Coppa Italia in 2003, a Supercoppa Italiana in 2004, and two UEFA Super Cups in 2003 and 2007, as well as playing a key role in Milan's first ever FIFA Club World Cup title in 2007. During this period, Milan also finished as runners up in Serie A in the 2004–05 and the 2005–06 seasons, as well as finishing second on penalties in the 2003 Supercoppa Italiana, and in the 2003 Intercontinental Cup.

At international level, Pirlo is the fifth-most capped player in the history of the Italian national team with 116 caps between 2002 and 2015. He played for the Italian youth teams at U15, U18 and U21 level, captaining and leading the latter to victory in the 2000 UEFA European Under-21 Championship as the Golden Player and Top Scorer of the tournament. He joined the Italian senior team in September 2002 and captained the Olympic team to a bronze medal in the 2004 Olympics. Later, he was instrumental in the senior team's victory in the 2006 FIFA World Cup. He was named Man of the Match three times, including the final, more than any other player in the tournament, and ultimately won the Bronze Ball (awarded to the third best player of the tournament) also being elected to the Team of the Tournament. He was also elected as part of the UEFA Euro 2012 Team of the Tournament after leading Italy to the final, winning three Man of the Match awards in the process, the most of any player along with Andrés Iniesta. He has also represented the Italian senior team at the 2004 and 2008 UEFA European Championships, the 2010 and 2014 FIFA World Cups and the 2009 and 2013 FIFA Confederations Cups, finishing third in the latter edition in Brazil, where he was also elected to the Team of the Tournament.

Pirlo led Serie A in the 2002–03 season in four categories – passes played (2589), ball possession (123 hours played and 39 minutes), successful balls (661), and successful passes (2093); he averaged almost 90 passes per game throughout the season. During this season, his second with the club, he also managed a career best of 9 goals in Serie A, as Milan finished the league in third place, also winning the Coppa Italia over Roma, and the UEFA Champions League, beating out Italian rivals and 2003 Serie A champions Juventus in the final 3–2 on penalties, following a 0–0 draw after extra-time. The following season saw Pirlo win the 2003 UEFA Super Cup with Milan over Porto, although the Rossoneri lost to Juventus on penalties in the 2003 Supercoppa Italiana following a 1–1 draw after extra time; during the match, Pirlo scored on a penalty in extra time, and once again in the shoot-out. Milan would also miss out on the 2003 Intercontinental Cup, losing out on penalties once again, to Boca Juniors, following a 1–1 draw after extra-time; on this occasion, Pirlo missed his penalty in the shoot-out, after previously setting up Milan's opening goal of the match. Pirlo would celebrate winning his first Serie A title with Milan during the 2003–04 season however, following up the scudetto with the 2004 Supercoppa Italiana over Lazio.

Pirlo made his Italy senior debut on 7 September 2002 under Giovanni Trapattoni, at the age of 23 in a 2–0 away win over Azerbaijan in a Euro 2004 qualifying match; he also appeared in a friendly match in Pescara against Turkey on 20 November, later that year, which ended in a 1–1 draw. Pirlo scored his first goal for Italy from a free kick in a 4–0 away win in a friendly match against Tunisia. His first major tournament with the Italian senior team was UEFA Euro 2004 under Trapattoni, where he made two appearances in Italy's last two group matches: the first in a 1–1 draw against Sweden, and the second in a 2–1 win over Bulgaria. The Italian team was eliminated in the first round, on direct encounters, following a three-way five-point tie with Sweden and Denmark.

Due to his performances with Brescia, Pirlo was spotted by Inter Milan coach Lucescu, who signed the playmaker. Pirlo was unable to break into the first squad permanently, however, and Inter finished eighth in the 1998–99 Serie A campaign. Inter loaned Pirlo to Reggina for the 1999–2000 season, alongside young Inter teammates Roberto Baronio and Mohamed Kallon. After an impressive season, he returned to Inter but was once again unable to break into the first team, making just four league appearances. He spent the second half of the 2000–01 season on loan at his former club, Brescia, where he played alongside his childhood idol, offensive playmaker Roberto Baggio. As Baggio occupied the attacking midfield role for Brescia, manager Carlo Mazzone made a ground-breaking decision, becoming the first coach to deploy Pirlo as a deep-lying playmaker, rather than as an offensive midfielder, a deeper creative role in which he particularly excelled, due to his long passing ability. Despite initially struggling against relegation that season, Brescia would eventually manage a comfortable seventh-place finish in Serie A, also reaching the Coppa Italia quarter-finals, qualifying for the 2001 Intertoto Cup. A notable moment in Pirlo's Brescia career was his long pass which assisted Baggio's late equaliser against Juventus at the Stadio delle Alpi, on 1 April 2001.

After three seasons on the Inter books, Pirlo was sold to rivals A.C. Milan for 33 billion Italian lire (€17,043,078) on 30 June 2001, the last day of 2000–01 financial year. The transfer fee was partially funded by the movement of Dražen Brnčić in the opposite direction for an undisclosed fee. In the same window Inter swapped Cristian Brocchi (25 billion lire; €12.9 million) for Guly (undisclosed fee; €8.537 million profit) and Matteo Bogani for Paolo Ginestra. The deals were later reported by the Italian press to have been undertaken to create "false profit" by inflating the players' values in the transfer fees in the swap deal. The exchange involving Ginestra and Bogani created an approximate €3.5 million "profit" for both clubs, but this actually manifested itself in terms of useless registration rights.

Pirlo made his Milan debut on 20 September 2001, in a 2–0 win over BATE Borisov in the UEFA Cup, after coming on for Massimo Donati. During his first season with the club, he helped the team to a fourth-place finish UEFA Champions League qualification spot, also reaching the semi-final of the UEFA Cup, the club's best ever result in the competition. On 30 March 2002, he scored his first goal with Milan in a 3–1 home win over Parma, from a free kick.

Pirlo is one of two children along with his brother Ivan. Pirlo and his wife Deborah Roversi married in 2001 and have two children: son Niccolò (born 2003) and daughter Angela (born 2006). In 2014, Pirlo and Roversi divorced after thirteen years of marriage, following Pirlo's affair with Valentina Baldini, a woman he met at his golf club.

Pirlo captained Italy to an Under-21 European Championship in 2000, wearing the number 10 jersey, and winning the awards for best player and top scorer of the tournament with three goals; he scored both goals – one from a penalty and the other from a free kick – in Italy's 2–1 victory over Czech Republic in the final. He also led the Italy under-21 team to a semi-final finish in the 2002 edition of the tournament. Pirlo played for Italy at the 2000 Summer Olympics in Sydney, scoring a goal in Italy's 1–0 opening win over hosts Australia on 13 September; he also helped Italy win the bronze medal at the 2004 Summer Olympics in Athens. With 46 matches and 16 goals, Pirlo is the record appearance holder for the Italian under-21 team, and the second highest goal-scorer after Alberto Gilardino.

Pirlo began his club career as an attacking midfielder with his hometown club Brescia, whom he helped win a Serie B title and subsequent promotion to Serie A in 1997. His promising performances led to a move to Inter Milan in 1998, but he struggled to gain playing time at his new club, and was sent on loan in 1999. Despite successful spells with Reggina and a return to Brescia, Pirlo was still unable to break into Inter's starting line-up and was sold to cross-city rivals A.C. Milan in 2001. At Milan, manager Carlo Ancelotti decided to transition Pirlo into a deep-lying playmaker to orchestrate the team's attacks. Pirlo excelled in his new role and soon developed into a world-class midfielder, and won a plethora of trophies, including two UEFA Champions Leagues, two UEFA Super Cups, two Serie A titles, a FIFA Club World Cup, a Supercoppa Italiana, and a Coppa Italia. After joining Juventus on a free transfer in 2011, who had gone trophyless since 2003, he added four more Serie A titles, which he won consecutively, as well as two Supercoppa Italiana titles, and a Coppa Italia. After playing in Italy for over 20 seasons, Pirlo joined Major League Soccer franchise New York City in 2015, helping the team to reach the playoffs in his second and third seasons before retiring in 2017.

Pirlo was born in Flero, Italy, in the province of Brescia. He began his career with the Flero youth team, later moving to Voluntas, and subsequently joined the youth sector of local club Brescia in 1994, where he initially played predominantly as a supporting forward. In 1995, at the age of 16, Pirlo made his Serie A debut for Brescia against Reggiana, on 21 May, becoming Brescia's youngest player to make an appearance in Serie A. He was promoted by his coach Mircea Lucescu. The following season, he did not appear with the senior team, although he was able to capture the Torneo di Viareggio with the youth team. After breaking into the Brescia first team during the 1996–97 Serie B season, he helped the club to gain Serie A promotion the following season by winning the Serie B title. He scored his first goal in Serie A during the 1997–98 season, in a 4–0 home win over Vicenza on 19 October 1997.

Pirlo's father founded a metal trading company in Brescia in 1982 called Elg Steel. Pirlo himself retains a stake in the family business. With regard to his wealth from his family business and footballing career, Pirlo stated in an interview with Italian Vanity Fair magazine that he never talks about money. Pirlo is known for being a wine connoisseur and he also runs his own vineyard in Italy, which produces around 15–20,000 bottles a year.

Andrea Pirlo Ufficiale OMRI (Italian pronunciation: [anˈdrɛːa ˈpirlo] ; born 19 May 1979) is an Italian former professional footballer. Pirlo was usually deployed as a deep-lying playmaker in midfield for both his club and national teams and he is widely regarded as one of the greatest ever exponents of this position due to his vision, ball control, technique, creativity and passing ability, as well as for being a free-kick specialist.