On 6 July 2009, as the Milan team reunited for pre-season training, Ambrosini was officially named club captain, inheriting the armband from Paolo Maldini. On 8 September 2009, he added one more year to his contract, extending his stay with the team at least until 2011. He won the Serie A title in 2010–11 season with three games in hand, edging out city rivals Internazionale. On 19 May 2011, he signed a new, one-year contract. After a disappointing second-place finish in the 2011–12 season and the departure of fellow team greats Filippo Inzaghi, Alessandro Nesta, Gennaro Gattuso, and Clarence Seedorf, Ambrosini was reported to be considering his future with the club, but Adriano Galliani was able to convince Massimo to sign yet another one-year deal and continue on to be the captain for Milan for the 2012–13 season. After a very rough start with several notable defeats, Milan eventually finished the season in the third place behind the defending champions Juventus and runners-up Napoli, securing a spot in the next season's Champions League qualification play-off.