winners (1): 2010-11
golden bench: 2008–09
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. 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.
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.
he was released from his contract by cagliari on 17 june, 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 ac milan. in his first season in charge, allegri led ac milan to their first championship title since 2004, beating inter in both league fixtures, however, his side failed to make it past the semi-finals of the coppa italia, by losing to u.s. citta di palermo 4-3 on aggregate in his first season. the team also qualified for the second round of the champions league, where they were eliminated by tottenham hotspur. however, massimiliano allegri has proven to the serie a that he's a promising young coach.