AC Milan Ambrosini began his career with
Cesena and graduated to their first team at the age of 17 during the
1994–95 season.
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, Ambrosini was given a handful of games as the team romped to the
Serie A championship. Used in the
1996–97 season only sporadically, Ambrosini was sent on
loan to
Vicenza, where he was given a spot in the team's starting line-up almost immediately, and helped his team avoid relegation at the end of the season. He also reached the semi-final of
UEFA Cup Winners' Cup with Vicenza. Recalled to the
San Siro, Ambrosini at last made a first-team place his own as Milan won back the Serie A championship in
1999. A regular the following term, he then saw his chances limited by a troublesome
knee injury before returning to full fitness to help Milan win the
Coppa Italia (scoring in a 4–1 win in the first leg of the
final over
Roma) and the
UEFA Champions League during the
2002–03 season, where he replaced
Rui Costa in the 87th minute of the
final against
Juventus, held at
Old Trafford. In
2003–04, although unable to establish himself as a first-team starter due to a series of niggling injuries and a loss of form, Ambrosini made 20 Serie A appearances – predominantly as a
substitute – and scored one
goal as Milan captured their 17th Serie A championship. In March 2005, he renewed his contract to June 2008. In
2004–05, he struggled to break into Milan first team, making only made 22 Serie A appearances and scoring one goal. It is his late goal, however, that took Milan to the UEFA Champions League final. With Milan losing 2–0, a scoreline which would have sent the match to
extra time as Milan defeated
PSV with the same score in the
San Siro, Ambrosini scored a header in second half
injury time to bring the score to 2–1 and give Milan the 3–2
aggregate lead. PSV immediately responded with a goal of their own to tie the aggregate score at 3–3, but Milan advanced to the
final on the
away goals rule. Ambrosini, however, missed the final in
Istanbul with yet another
injury as Milan were defeated on
penalties by
Liverpool. In
2005–06, he again suffered a series of
injuries which limited him to just 13 Serie A appearances and one goal, thus making him out of contention for the
Italian squad for the
2006 FIFA World Cup in Germany. Unlike the previous seasons,
2006–07 became Ambrosini's late breakthrough as he had fully recovered from his recurring injuries. Although not an immediate starter at the beginning, following a series of stunning performances, he eventually made his way into the team's starting 11, prompting
Carlo Ancelotti to change his preferred formation from
4–3–1–2 to
4–3–2–1 (alternatively,
4–4–1–1), in which he would play a left-sided
defensive midfielder, in a role similar to that of
Gennaro Gattuso responsible for winning back possession and passing the ball to either a
deep-lying playmaker Andrea Pirlo or other attacking players. He scored two decisive goals in Serie A against
Sampdoria and
Atalanta, both with his head. He was also a key member to Milan's victory over
Bayern Munich and
Manchester United in the UEFA Champions League, balancing the game for Milan through his vision and leadership skills; his long pass from his team's half of the pitch to an unmarked striker
Alberto Gilardino helped ensure Milan's eventual 3–0 victory as Gilardino scored a goal that drastically reduced Manchester United's chances of a comeback. This game also prompted Ambrosini to change his mind about leaving Milan due to lack of playing time and extend his contract until June 2010. Later that month, Ambrosini started in the
final of the
2006–07 Champions League and played a strong game in Milan's eventual 2–1 win over Liverpool. He was also the last player to touch the ball seconds before the final whistle. In
Paolo Maldini's absence, Ambrosini was once again the
stand-in captain for the
European Super Cup Final against
UEFA Cup winners
Sevilla FC, which Milan won 3–1. Ambrosini was Milan captain in the absence of Paolo Maldini throughout the
2007–08 campaign. In this campaign, Ambrosini scored four goals. He scored decisive goals against
Palermo and
Empoli, and played very well in the home leg of the
Milan derby against
Internazionale on 4 May 2008, setting up the second goal for teammate
Kaká and putting in an excellent performance throughout the game, which Milan won 2–1. However, Milan had failed to earn 3 points in each single game leading up to a 4–1 win against
Udinese on the final day of the season, thus finishing only in fifth place and qualifying for
2008–09 UEFA Cup instead of the desired Champions League. During the
2008–09 campaign, Ambrosini was once again a regular fixture in the Milan starting lineup, making 26 appearances in the team's Serie A campaign. During a
pre-season friendly tournament against
Juventus, Ambrosini was named
Man of the Match as he
netted twice to secure a Milan victory. His second goal was a superb effort into the roof of the net, past a bewildered
Alex Manninger. This season was also memorable for him as he had managed a season total of eight goals (one in the UEFA Cup), more than he has scored in any season in his career with Milan. The goals included a brilliant header off
David Beckham's
free kick against
Lazio, and a well-placed goal in a 5–1 win over
Torino. Ambrosini also scored his first double in a competitive fixture in a 3–2 loss to
Roma during Paolo Maldini's final home game, and received a standing ovation from the home crowd despite being
sent off by the
referee for a second
yellow card. 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. On 11 June 2013, Milan CEO
Adriano Galliani confirmed that the club had decided not to extend Ambrosini's expiring contract, thus ending his eighteen-year stay at Milan.
Fiorentina On 4 July 2013
Fiorentina confirmed on their official website that they had won the race to sign Ambrosini on a one-year deal, beating
West Ham United who were also looking to sign him. He 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. ==International career==