Nyorai mberi kweiyi ndima - Maldini akatanga mwaka unotevera nekusimudza 2004 Supercoppa Italiana
somutungamiriri pashure pokunge Milan yarova Lazio. Milan yakapedza yechipiri muSerie A kuJuventus mwaka iwoyo, uye yakasvika muChampions League yekupedzisira, chete kuti ikanganise pazvipingamupinyi kuLiverpool, kunyange zvazvo Maldini akazarura zvibodzwa muminiti yekutanga. Muna 2005, Maldini akasarudzwa kuti ave chikamu cheEFAFA Team of the Year kechipiri mubasa rake, uye akasarudzwawo kuti ave chikamu cheFIFPro World XI kekutanga mubasa rake. Mwaka wakatevera, Milan yakapedza iri yechipiri kuseri kweJuventus muSerie A zvakare, uye yakasvika kuma semi-fainari eChampions League, kungokundwa nemakwikwi ekupedzisira Barcelona. Zvose Juventus neMilan vakazobviswa mapoinzi nekuda kwekubatanidzwa mu2006 "Calciopoli" match fixing scandal, uye zita rakapihwa kuInternazionale, nepo Juventus yakadzikiswa, neMilan ichipedza iri pachinzvimbo chechitatu mushure mekubviswa mapoinzi. Munguva yemwaka, Maldini akarova yake yekutanga uye chete kaviri yebasa rake, achipesana naReggina. Musi wa 25 Gunyana 2005, Maldini akaputsa Dino Zoff's Serie A kuoneka rekodhi mushure mekutamba mutambo wake we 571st weligi vachipesana neTreviso; mazuva manomwe apfuura, akange atamba mutambo wake we800 mumakwikwi ese eMilan.