Massimo Ambrosini - Club Career

Club Career

Ambrosini began his career with Cesena and graduated to their first team at the age of 17 during the 1994–95 season. 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. Only used marginally more in 1996–97, Ambrosini was sent on loan to Vicenza, where he was a key member of the team that successfully preserved their Serie A status. 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 and UEFA Champions League, where he replaced Rui Costa in the 87th minute 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 at the San Siro, committing himself until June 2008.

In 2004–05, he struggled to break into Milan first team, and only made 22 Serie A appearances, scoring one goal. However, it is his late goal 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 immedeately 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. However, Ambrosini 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 Italy squad for the 2006 FIFA World Cup in Germany.

In 2006–07, Ambrosini fully recovered from his injury. He was not an immediate first-team choice, but following a series of stunning performances, he eventually made it and forced Carlo Ancelotti to change his formation from 4–3–1–2 to 4–3–2–1 (alternatively, 4–4–1–1). He has scored two decisive goals from his head in Serie A, against Sampdoria and Atalanta B.C.. 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. It was also his vision that ensured Milan a place in the final. Having stolen the ball from Manchester United, Ambrosini immediately passed to a free Alberto Gilardino. Gilardino scored to make it 3–0, thus ending United's hope of winning the trophy.

Ambrosini originally intended to join Fiorentina due to lack of first-team choice, but changed his mind after the Champions League semifinal against Manchester United. He renewed his contract with Milan until 2010. Shortly after, he started in the final of the 2006–07 Champions League and played a strong game in Milan's 2–1 win over Liverpool. 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 Inter on 4 May 2008, setting up the second goal for team-mate Kaka and putting in an excellent performance throughout the game, which Milan won 2–1. Unfortunately, despite winning 4–1 against Udinese on the final day of the season, Milan could only finish fifth and qualify for the UEFA Cup 2008-09.

During the 2008–2009 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 the 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 8 goals (1 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 brace 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 current contract to 2011. He won Serie A title in 2010–11 season with 3 more games to play. On 19 May 2011, he signed a new 1-year contract. After the disappointing second place finish in the 2011–12 season and the departure of fellow greats such as Filippo Inzaghi, Alessandro Nesta, Gennaro Gattuso and Clarence Seedorf, Ambrosini was reported to be considering his future but Galliani was able to convince Massimo to sign yet another 1 year deal and continue on to be the captain for A.C. Milan in the 2012–13 season.