Maldini a jucat în cariera sa doar pentru AC Milan, în perioada 1985-2009, strângând 647 de meciuri şi 29 de goluri în tricoul ”bianco-nerilor”. În cei 14 ani în care a evoluat pentru naţionala Italiei, el a acumulat 126 de elecţii şi 7 goluri.
Palmaresul său cuprinde şapte titluri de campion al Italiei (1987–88, 1991–92, 1992–93, 1993–94, 1995–96, 1998–99, 2003–04), o Cupă a Italiei (2002-2003), cinci Supercupe ale Italiei (1988, 1992, 1993, 1994, 2004), cinci Cupe ale Campionilor Europeni / Ligi ale Campionilor (1988–89, 1989–90, 1993–94, 2002–03, 2006–07), cinci Supercupe ale Europei (1989, 1990, 1994, 2003, 2007), două Cupe Interconctinentale (1989, 1990) şi un Campionat Mondial al Cluburilor (2007). La nivel de naţională, italianul stă mai ”slab”: vicecampion mondial (1994) şi locul trei la CM (1990) şi vicecampion european (2000).
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