9. Filippo Inzaghi
Filippo 'Pippo' Inzaghi, currently managing a Benevento side that he steered to a Serie B title in his first season in charge, was once one of the best strikers in Italy.
321 goals and assists in 604 games says it all.
Inzaghi joined Milan in 2001 when he was 27 and few would have expected that he would see out a further 11 years and 300 games at the Rossoneri.
During his time at the club, he managed to win 2x Champions League, 2x Serie A, 1x Italian Cup, 1x FIFA Club World Cup, 2x UEFA Super Cup and 1x World Cup, scoring in four finals en route to this haul of silverware.
As his playing days came to a close Inzaghi endured a spell of injuries, including cruciate ligament damage and multiple strains.
His latest injury looked set to force his career into a drab ending, but a 23-minute substitute appearance on the final day of the 2011/12 season was enough time to earn him the final goal of his career with the match-winner in a 2-1 victory over Novara.
This win guaranteed Milan a 2nd place league finish and Champions League football. What a way to bow out.