Mushure mekuonekwa kuItaly pasi paGiovanni Trapattoni panguva yavo ye2002 FIFA World Cup yekukwikwidza mushandirapamwe, Montella akasarudzwa senhengo yechikwata cheItaly icho chaizokwikwidza ku2002 World Cup, uko maItaly akabviswa zvine nharo mumutambo we16 kuenda kuSouth Korea mushure mekukundwa 2<unk>1 munguva yekuwedzera. Mumutambo wake chete weWorld Cup, panguva yemutambo wekupedzisira weItaly kupokana neMexico mu2002 World Cup, akarasikirwa nechinangwa zvisirizvo. Gare gare akaisa Del Piero's equalizer mune yekupedzisira 1<unk>1 dhizaini, iyo yakabatsira Italy kufambira mberi kuenda kunharaunda yechipiri. Akanga apisa uye akanga agadzirira kubuda pabhenji mumutambo wechikamu che16, asi Ahn wekuSouth Korea akarova chinangwa chegoridhe nguva pfupi asati atanga kupinda. Gare gare akaonekwawo kuItaly mumitambo mitatu yeEuro 2004 yekukodzera, asi haana kudaidzwa kumakwikwi ekupedzisira
. Akaita chitarisiko chake chekupedzisira cheItaly pasi paMarcello Lippi, mumutambo wepasi rose wekushamwaridzana neRussia musi wa9 Kukadzi 2005, wakaitirwa muCagliari, iyo Italy yakakunda 2 <unk> 0. Pakazara, Montella akahwina makapu makumi maviri uye akarova zvibodzwa zvitatu zveItari.