Career
Player career:
After spending the earlier part of his career in the lower leagues, including his hometown club Livorno, Allegri joined Pescara in 1991. He established himself in midfield as Giovanni Galeone's side won promotion to Serie A in 1992. Allegri was an outstanding performer for Pescara in Serie A. Despite the side's relegation in last place, there was no shortage of goals and Allegri scored an impressive 12 goals from midfield. He moved on to Cagliari and then Perugia and Napoli before returning to Pescara. Brief spells at Pistoiese and Aglianese followed before his retirement from active football in 2003.
He was banned for one year in 2001 with others six Italian footballers for match-fixing following a Coppa Italia tie in 2000. The Italian Football Federation (FIGC) also handed one-year suspensions to Fabio Gallo, Sebastiano Siviglia, and Luciano Zauri of Serie A side Atalanta; and Alfredo Aglietti of Serie B's Pistoiese.
Coach career:
Allegri started a coaching career in 2004, serving as boss of Serie C2 team Aglianese, the club where he spent his two final years as a player. Following an impressive season with them, Allegri was called to head Grosseto, then in Serie C1; his experience with the biancorossi, however, proved not to be as successful as with Aglianese, and he was ultimately sacked shortly after the beginning of the 2006–07 Serie C1 season. Shortly after being sacked by Grosseto, Allegri agreed to rejoin his mentor Giovanni Galeone at Udinese, becoming part of his coaching staff. This practice, however, proved to be forbidden by the Italian football laws because he was still contracted with the Tuscan club, which caused Allegri to be disqualified for three months on early 2008.
On August 2007, Allegri became head coach of ambitious Serie C1 team Sassuolo, who Allegri managed to lead quickly into the top league spots. On 27 April 2008, Sassuolo mathematically ensured the 2007–08 Serie C1/A league title, thus winning a historical first promotion to Serie B
On 29 May 2008, Allegri was announced as new head coach of Cagliari in the Serie A, replacing Davide Ballardini. Despite a disappointing start, with five losses in the first five league matches, Allegri was confirmed by club chairman Massimo Cellino and later went on to bring his team up to a mid-table placement in December.
Allegri was released from his contract by Cagliari on 17 June 2010, under request of Serie A giants Milan, who were interested in appointing him as their new head coach. On 25 June, Allegri was officially appointed as the new coach of Milan. In his first season in charge, Allegri led Milan to their first championship title since 2004, beating titel incumbents Internazionale in both league fixtures. His side, however, failed to make it past the semi-finals of the Coppa Italia, losing to Palermo 4–3 on aggregate. The team also qualified for the second round of the Champions League, where they were eliminated by Tottenham Hotspur.
On 13 January 2012, Allegri agreed to extend his contract with Milan to the end of 2013–14 season. On 5 June 2012, Allegri stated that he intends to coach for only 10 more years and plans to retire at the age of 55 due to the fact that coaching contains a high level of stress and anxiety. He also said that he hopes to coach the Italian national side before he retires.
At the beginning of the 2012-2013 season, Milan had only collected 8 points from their first 7 games, putting Allegri in danger of getting fired early on. Despite all the criticism from the critics, Milan stuck with Allegri and he managed to get the best out of the youth players including Stephan El Shaarawy, Mattia De Sciglio and later on Mario Balotelli. He managed to steer the Rossoneri from 16th place to finishing 3rd at the end of the season, with an epic 2-1 comeback away to Siena. That gave Milan the spot to play in the playoff round for the 2013-14 UEFA Champions League campaign. On June 2, 2013, Silvio Berlusconi confirmed Massimiliano Allegri to remain as Milan coach, despite numerous speculations that he would be given the sack and be replaced by former Milan player Clarence Seedorf.