Kammala jumla mai zuwa: Maldini ya fara kakar wasa ta gaba ta hanyar tayar da
2004 Supercoppa Italiana a matsayin kyaftin bayan Milan ta doke Lazio. Milan ta gama na biyu a Serie A zuwa Juventus a wannan kakar, kuma ta kai wasan karshe na gasar zakarun Turai, kawai don rasa a kan Liverpool, kodayake Maldini ya bude ci a minti na farko. A shekara ta 2005, an zabi Maldini ya zama wani ɓangare na UEFA Team of the Year a karo na biyu a cikin aikinsa, kuma an kuma zaɓe shi ya zama wani ɓangare na FIFPro World XI a karon farko a cikin aikinsa. A kakar wasa ta gaba, Milan ta kammala a matsayi na biyu a bayan Juventus a Serie A kuma, kuma ta kai wasan kusa da na karshe na gasar zakarun Turai, sai dai Barcelona ta doke ta. Dukansu Juventus da Milan daga baya an cire maki saboda sun shiga cikin abin kunya na "Calciopoli" na 2006, kuma an ba da lambar yabo ga Internazionale, yayin da Juventus ta sauka, tare da Milan ta kammala a matsayi na uku bayan an cire maki. A lokacin kakar, Maldini ya zira kwallaye na farko da na biyu a cikin aikinsa, a kan Reggina. A ranar 25 ga Satumba, 2005, Maldini ya karya rikodin Dino Zoff na Serie A bayan ya buga wasansa na 571 da ya buga da Treviso; kwanaki bakwai da suka gabata, ya buga wasa na 800 a duk gasa don Milan.