Dhameystir weedha soo socota: Maldini wuxuu bilaabay xilli ciyaareedkii xigay isagoo kor u qaadaya
2004 Supercoppa Italiana oo ah kabtan ka dib markii Milan ay ka adkaatay Lazio. Milan ayaa ku dhameysatay kaalinta labaad ee Serie A ee Juventus xilli ciyaareedkaas, waxayna soo gaareen finalka Champions League, kaliya waxay ka badiyeen ganaaxyada Liverpool, in kasta oo Maldini uu daqiiqadii ugu horreysay goolka furay. Sannadkii 2005, Maldini waxaa loo doortay inuu ka mid noqdo Kooxda UEFA ee Sanadka markii labaad ee xirfadiisa, waxaana sidoo kale loo doortay inuu ka mid noqdo FIFPro World XI markii ugu horreysay ee xirfadiisa. Xilli ciyaareedkii xigay, Milan ayaa mar labaad ku soo baxday Juventus Serie A, waxayna gaareen semi-finalka Champions League, kaliya waxaa laga badiyay horyaalkii ugu dambeeyay Barcelona. Labada Juventus iyo Milan ayaa markii dambe laga jaray dhibco ay ku lug lahaayeen 2006 "Calciopoli" fadeexada ciyaarta, waxaana horyaalka la siiyay Internazionale, halka Juventus ay hoos u dhacday, iyadoo Milan ay ku dhameysatay kaalinta saddexaad ka dib dhibcaha laga jaray. Intii lagu jiray xilli ciyaareedkii, Maldini wuxuu dhaliyay labadiisii kulan ee ugu horreeyay iyo kii kaliya ee xirfadiisa, ka hor Reggina. Bishii Sebtember 25, 2005, Maldini wuxuu jabiyay rikoodhka Dino Zoff ee Serie A ka dib markii uu ciyaaray kulankiisii 571aad ee horyaalka ee ka dhanka ah Treviso; toddobo maalmood ka hor, wuxuu ciyaaray kulankiisii 800aad ee tartamada oo dhan ee Milan.