 Mushure mekushanda semukuru scout wechikwata chake chekare cheMilan kubva muna Kukadzi 1999, Maldini akadzoka kwenguva pfupi kunodzidzisa timu yekutanga yeMilan munaKurume 2001, achishanda semaneja wenguva pfupi wekirabhu uyo kaputeni wake aive mwanakomana wake, Paolo padivi pemurairidzi wevechidiki Mauro Tassotti, zvichitevera kudzingwa kwaAlberto Zaccheroni, uye akatungamira timu kumitambo yavo yekupedzisira yemwaka. Kunyange zvazvo kirabhu yakatsungirira mwaka unovhiringidza, ichipedzisa munzvimbo yechitanhatu uye ichitadza kukwanisa kuenda kuChampions League, Maldini akatungamira timu kukunda kusingakanganwiki 6-0 pamusoro pevanokwikwidza vepakati peguta Inter muMilan Derby musi waMay 11; mhedzisiro yacho yaive yekurohwa kwakanyanya kweInter kumba muSerie A, uye kukunda kukuru kweMilan muDerby. Mushure mekubatsira kirabhu kuti ikwanise kuenda kuEFAFA Cup, Maldini akatsiviwa naFatih Terim mwaka unotevera, kunyange zvazvo pakutanga akaramba ari mukirabhu semupi wezano kumudzidzisi. 