Massimo Ambrosini

Massimo Ambrosini (born 29 May 1977) is an Italian former professional footballer who mainly played as a defensive midfielder.

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.

At international level, he represented Italy at the 2000 Summer Olympics, and in two UEFA European Championships, winning a runners-up medal at UEFA Euro 2000.

He currently works as a pundit and football commentator for Sky Sport Italia.

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 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 March 2005, he renewed his contract to June 2008.

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.

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.

At club level, he is mostly known for his successful time at Italian team AC Milan, where he spent eighteen years of his career, winning several titles, and captained the side from 2009 to 2013 following the retirement of Paolo Maldini.

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.

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.

He won the Serie A title in 2010–11 season with three games in hand, edging out city rivals Internazionale.

Ambrosini retired from professional football in 2014, after a season with Fiorentina.