 Nyorai kuenderera mberi kweiyi ndima - Pakutanga chigadzirwa chechidiki cheMilan, Maldini akaenderera mberi nekutamba rake rese kirabhu basa nechikamu chevakuru cheMilan. Akakunda Coppa Italia Primavera nechikwata chechidiki cheMilan mumwaka wa198485, uye akaita mutambo wake wekutanga weMilan pasi pemurairidzi Nils Liedholm mumwaka mumwe chetemusi wa 20 Ndira 1985, achitsiva akakuvara Sergio Battistini mumutambo wakanangana neUdinese aine makore gumi nematanhatu. Yakanga iri chitarisiko chake chega cheligi yemushandirapamwe, asi akabva angogadzirwa nhengo yechikwata gumi nerimwe mwaka unotevera, aine makore gumi nemanomwe, kurudyi-kumashure, achipihwa hembe nhamba 3, iyo yaimbovewo yababa vake, Cesare. Akazochinjirwa kunzvimbo yake inozivikanwa yekuruboshwe-kumashure nekuda kwekugona kwake nerutsoka rwake rweruboshwe. Maldini akaitawo Coppa Italia yake yekutanga muna 1985, musi wa21 Nyamavhuvhu, apo kutanga kwake mumakwikwi eEuropean kwakauyawo gare gare gore rimwe chetero, musi wa18 Gunyana. Akawana chinangwa chake chekutanga che29 muSerie A musi wa 4 Ndira 1987 mukukunda 10 kurwisa Como. 