 Trapattoni akaberekerwa muCusano Milanino pedyo neMilan, akaita basa rakabudirira semutambi ne AC Milan, achitamba semudziviriri wepakati kana semudziviriri wepakati ane basa guru rekuendesa bhora kune vamwe vatambi vakagadzira saGiovanni Lodetti naGianni Rivera. Akakunda mbiri Serie A mazita 196162, 196768 uye maviri European Cups 196263, 196869 panguva yake Milan, uye aiva mumwe nyeredzi 1963 European Cup Finalvachirwa naBenfica, vakabudirira kuisa Eusébio mucherechedzo wevarume muhafu yechipiri. Nenzira imwecheteyo, mukukunda kwechikwata 4-1 mu1969 European Cup Final vachipesana neAjax, akawana kurumbidzwa munhau dzeItaly nekuda kwekudzivirira kwake uye kugona kubvisa kutyisidzira kwekurwisa kwaJohann Cruyff. 