Milan again became a dominant force in Italy and in Europe under Carlo Ancelotti. In the 2001–02 season, Milan finished in fourth place, qualifying for the Champions League, and also reached their best ever finish in the 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. The following season, Maldini lined up with Alessandro Nesta, Alessandro Costacurta and Cafu, who, along with Jaap Stam during the 2004–05 season, formed a formidable defensive lineup in Italy and in Europe. Milan finished third in Serie A, but Maldini won the first Coppa Italia of his career, defeating Roma in the final. On 15 March 2003, he made his 500th appearance in Serie A.
Milan again became a dominant force in Italy and in Europe under Carlo Ancelotti. In the 2001–02 season, Milan finished in fourth place, qualifying for the Champions League, and also reached their best ever finish in the 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. The following season, Maldini lined up with Alessandro Nesta, Alessandro Costacurta and Cafu, who, along with Jaap Stam during the 2004–05 season, formed a formidable defensive lineup in Italy and in Europe. Milan finished third in Serie A, but Maldini won the first Coppa Italia of his career, defeating Roma in the final. On 15 March 2003, he made his 500th appearance in Serie A.