Massimo Ambrosini loyally donned the red and black colours for eighteen years amidst intense competition, numerous injuries and trying times to emerge as one of the truly honourable servants of AC Milan and the San Siro. Ambrosini always served and put the team first and it was an honour to see him wear the Captain's armband after the departure of Maldini as he led the team to the 2011 Scudetto - his fourth with the club.
Ambrosini was signed by Milan coach Fabio Capello in 1995 but did not really break into the first team until 1999. Ambrosini was a talented player but was plagued by minor recurring injuries that seriously limited his playing time allowing others such as Andrea Pirlo, Gennaro Gattuso and Demetrio Albertini. Despite his limited playing time, his tenacity and drive allowed him to be a leader amongst a team of super stars and earned cult status amongst Milan fans as one of the core players of a world conquering group. He always made himself available to contribute in critical campaigns such as both Champions League runs and the Coppa Italia victory as well as captaining the side to the 2010-11 Scudetto. Ambrosini's leadership was particularly evident when he managed to rally average Milan sides to Champions League spots in 2011-12 and 2012-13 despite many departures of Milan legends.
Achievements with Milan
- Serie A : 1995–96, 1998–99, 2003–04, 2010–11
- UEFA Champions League : 2002–03, 2006–07
- Coppa Italia : 2002–03
- Supercoppa Italiana : 2004, 2011
- UEFA Super Cup : 2003, 2007
- FIFA Club World Cup : 2007
Perhaps Ambrosini's top highlight outside of his defensive cleanliness was the goal he scored to win Milan their only Coppa Italia of the 21st Century against AS Roma in 2003. Ambrosini connected brilliantly with his head from a Rivaldo free kick to get Milan's second goal of a 4-1 rout. Watch this highlight and some others here or below.