Nyora kupfuurira kweiyi ndima - Mwaka wa2002-03, wekutanga waTomasson kuMilan, wakavaona vachikunda mukombe weItaly. Tomasson aiwanzoshandiswa sechinzvimbo chekupedzisira, asi akakwanisa kurova zvibodzwa zvitatu muEFAFA Champions League; uye nokudaro akabatawo mugove wake wechikwata, apo Milan yakakunda mutambo wakakurumbira muna May 2003. Tomasson akarasikirwa nemagumo nekuda kwekukuvara kwaakawana mumutambo wekutanga we2003 Coppa Italia Final. Mumwaka wa2003-04, Tomasson akapihwa nguva yakawanda yekutamba uye akakwanisa kurova zvibodzwa gumi nezviviri muSerie A mumushandirapamwe wekukunda. MunaAugust 2004, aivewo chikamu chechikwata cheMilan chakakunda Italian Super Cup
, nekukunda 3-0 vachipesana neCoppa Italia makwikwi Lazio.