1. AC Milan coach Fabio Capello then won the race to sign him the following year, and despite facing tough competition to break into the all-star Milan side, Massimo Ambrosini was given a handful of games as the team romped to the Serie A championship.
Massimo Ambrosini reached the semi-final of UEFA Cup Winners' Cup with Vicenza.
Massimo Ambrosini missed the final in Istanbul with yet another injury as Milan were defeated on penalties by Liverpool.
Massimo Ambrosini scored two decisive goals in Serie A against Sampdoria and Atalanta, both with his head.
Massimo Ambrosini was the last player to touch the ball seconds before the final whistle.
Massimo Ambrosini's second goal was a superb effort into the roof of the net, past a bewildered Alex Manninger.
On 6 July 2009, as the Milan team reunited for pre-season training, Massimo Ambrosini was officially named club captain, inheriting the armband from Paolo Maldini.
On 11 June 2013, Milan CEO Adriano Galliani confirmed that the club had decided not to extend Massimo Ambrosini's expiring contract, thus ending his eighteen-year stay at Milan.
Massimo Ambrosini made 30 appearances for Fiorentina in his first season with La Viola, helping the club to fourth place in Serie A Massimo Ambrosini would announce on 21 May 2014 that he would be leaving Fiorentina after one season.
Massimo Ambrosini made his senior international debut on 28 April 1999 against Croatia, under manager Dino Zoff, and was part of the Italian squad at UEFA Euro 2000, which ended with an appearance as a substitute in the final loss to reigning World champions France following David Trezeguet's golden goal; he represented Italy at the 2000 Summer Olympics under Marco Tardelli later that year, where Italy were eliminated in the quarter-finals by eventual finalists Spain.
Massimo Ambrosini was unavailable for selection for the 2002 FIFA World Cup finals under Giovanni Trapattoni due to injury, and then failed to break into the squad for the UEFA Euro 2004 finals.
Massimo Ambrosini was then called up by the national side's manager to Italy's squad for UEFA Euro 2008 in Austria and Switzerland, appearing in all four of his nation's matches throughout the tournament, as Italy were eliminated in the quarter-finals of the tournament by eventual champions Spain, following a penalty shootout.
Massimo Ambrosini is married to an Italian woman, Paola Ambrosini.