[24] 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.

[26][29] Despite initially struggling against relegation that season,[30] 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.

[31] 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.

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.

[59][60] 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.

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.

[96] 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.

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.

[125] 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.

[127] 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.

[129] 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.

[136] On 6 July 2015, it was announced that Pirlo had completed a move to Major League Soccer (MLS) expansion franchise New York City FC as their third Designated Player.

[135][137][138] In doing so, he became the highest paid Italian player in all leagues with an $8 million salary,[citation needed] until Graziano Pellè overtook him after moving to Chinese club Shandong Luneng the following year.

[147] 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.

[144] 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.

[157] 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.

[167] 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.

[174] 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.

[180] 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.

[183][184] 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.

[193][194] 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.

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".

Together with Baggio, I think he's the greatest talent that Italian football has produced in the last 25 years.Pirlo spots a pass in a split-second that lesser players could spend a whole lifetime waiting to see.Pirlo can make his feet do whatever he wants.

[241][242][243][244] Although not gifted with pace, stamina, physicality or notable defensive skills, work-rate, or tackling abilities,[nb 1] Pirlo was known for his composure in possession, and drew praise for his touch, technique, balance, elegance, close control, and dribbling ability, as well as his flair and creativity in beating players with feints during one-on-one situations, in order to retain the ball and create space for himself to play and receive passes.

[256][268][269] Throughout his career, he was regarded as one of the best free-kick takers in the world,[256][270] and drew praise from pundits for his versatility, and ability to both score and create chances from dead-ball situations.

[246][271][272][273] He was extremely effective at curling shots accurately on target from close range,[267] a technique that he perfected by studying Baggio in training sessions during their time at Brescia together;[267] as a youngster, Zico, Michel Platini, and Diego Maradona were also some of his major influences when taking free kicks.

[131][278] Fellow players on the Italy national team nicknamed Pirlo l'architetto ("the Architect"), because of the way that he built plays, and set up goal-scoring opportunities with long, lobbed through passes.

[291] Pirlo cited the teams that "inspired [his] idea of football" as "the Barcelona of Johan Cruyff and then of Pep Guardiola, the Ajax of Louis van Gaal, the Milan of Carlo Ancelotti, and the Juventus of Antonio Conte".

[310] 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.

[313][314] 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.