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#5 Alessandro Costacurta (AC Milan): 5 Titles
Years won: 1988/89, 1989/90, 1993/94, 2002/03, 2006/07
If there ever was a centre-back AC Milan could depend on, it was Alessandro Costacurta. The Italian defender's career spanned 21 years and, barring a season on loan at Monza, he played with the red-and-black stripes of the Rossoneri.
Alongside Mauro Tassotti, Franco Baresi, and Paolo Maldini, they formed arguably the greatest back-line in Italy and Europe in the late '80s and early '90s. He was a versatile defender capable of playing in numerous positions and was well known for his timing in the tackle.
He made 663 appearances for the club in all and was a force to reckon with. A centre-back by trade, he even played as a makeshift right-back, most notably in the 2003 final against Juventus.
With Alessandro Nesta and Paolo Maldini playing as centre-backs, Costacurta played on the right side of the defence and helped Milan keep a clean sheet as he kept Gianluca Zambrotta in check while also helping Nesta deal with Edgar Davids and Alessandro Del Piero.
From his first European title in 1989 to his last in 2007, Costacurta has won the trophy in three different decades. However, he wasn't in the squad for two finals (1994 and 2007).
