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Style of play [ ] A physically strong, tenacious, energetic, and hardworking , , or , with a wide range of skills, Ambrosini was well regarded for his ability in the air, and was capable of being a goal-threat, in particular from set-pieces, due to his height, elevation, ability to make attacking runs into the area, and his heading accuracy, as well as his powerful striking ability from distance, which even led manager Carlo Ancelotti to deploy him as a on occasion.

In , he struggled to break into Milan first team, making only made 22 Serie A appearances and scoring one goal.

Carlo Laudisa 19 December 2003.

Pietro Mazzara 22 November 2011.

La Gazzetta dello Sport in Italian.

He scored decisive goals against and , and played very well in the home leg of the against on 4 May 2008, setting up the second goal for teammate and putting in an excellent performance throughout the game, which Milan won 2—1.

In March 2005, he renewed his contract to June 2008.

Under subsequent manager , he was also excluded from the national side and was not called up for the , which Italy went on to win.

During the , Ambrosini was once again a regular fixture in the Milan starting lineup, making 26 appearances in the team's Serie A campaign.