 Nyorai kupfuurira kweiyi ndima - Muna 1999, Shevchenko akabatana nekirabhu yeItaly AC Milan pamutengo wepamusoro-soro panguva iyoyo wemadhora 25 miriyoni. Akaita mutambo wake wekutanga weligi musi wa28 Nyamavhuvhu 1999 mumutambo we2x2 neLecce. Pamwe chete nevamwe vatambi vashanu Michel Platini, John Charles, Gunnar Nordahl, István Nyers, naFerenc Hirzer akakwanisa, semutambi wekunze, kuhwina mukombe weSerie A scoring mumwaka wake wekutanga, achipedza aine zvibodzwa makumi maviri nezviviri mumitambo makumi matatu nemaviri. Shevchenko akachengeta chimiro chake chakanakisa mumwaka wa2000-01, achihwina zvibodzwa makumi maviri nezvina mumitambo makumi matatu nemana, kusanganisira zvibodzwa zvipfumbamwe mumitambo gumi nemana yeChampions League. Mumwaka mumwe chetewo, akasanganazve naKakha Kaladze sevadzidzi vechikwata apo Milan yakasaina mudziviriri weGeorgia kubva kuDynamo Kyiv muna Ndira 2001. 