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.

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 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 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.
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.
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 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 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.
Andrea Pirlo