#4 Filippo Inzaghi
Filippo Inzaghi signed for the Diavolo from Juventus in 2001 for a reported fee of €37 million. The former Italy international had a slow start to life in Milan as his first season was marked with injuries - making just 20 appearances.
However, things turned around in his second season as he formed a deadly partnership with Andriy Shevchenko.
Inzaghi overcame knee problems and ended the season with 12 goals in 22 appearances during the '04/05 campaign.
Pippo finished his career at the San Siro in 2012 at the age of 39 - making 300 appearances for the club and scoring 126 goals for the Red and Black. He won eight major honors with the club.
Inzaghi returned as a manager in 2014 but only lasted a year as the club finished tenth in the league under his guidance.