20. Paolo Maldini
The only defensive position Maldini hardly ever occupied was right-back – despite it being where he started out playing. Having broken into the Milan side at 16 years old in January 1985, Maldini hung up his boots in May 2009 following more than 1000 matches for club and country in his near 25-year career.
He won seven Scudetti and a remarkable five European Cup/Champions League trophies. When he retired, Milan retired his No.3 shirt – which will only ever be worn again if one of his sons plays for the Rossoneri.
Career highlight: Maldini was part of not just one but two of the all-time great defensive partnerships, with Franco Baresi and then Alessandro Nesta. It was his achievements alongside the former with an unbeaten title-winning campaign, that arguably rank at the top of a remarkable CV.