 Ventola akasaina kuInter Milan mumwaka wa19981999, akaita makwikwi makumi maviri nerimwe, uye akarova zvibodzwa zvitanhatu, achitamba pamwe chete nevamwe vatambi vakakurumbira, vakaita saRonaldo, Roberto Baggio, Iván Zamorano, Andrea Pirlo, uye Youri Djorkaeff, kunyangwe zvakanyanya semutsivi. Munguva yemwaka, akaratidza kugona chaiko kweyechidiki zera rake, akarova zvibodzwa gumi nerimwe mumakwikwi ese, pamwe nechinangwa kurwisa vakundi veEuropean Cup Manchester United mumakota-fainari e1998-1999 UEFA Champions League. Zvisinei, gore rimwe chete gare gare akasayina chibvumirano chekubatana neBologna mushure mekutamisa kwaChristian Vieri 32 mamirioni kuInter Milan kubva kuLazio uye gare gare Atalanta mumwaka miviri inotevera, muchibvumirano chekuchinjana naCorrado Colombo. Munguva yake yechikwereti neBologna, akaita 14 kuoneka muSerie A, pasina kugovera chinangwa, kunyange zvazvo akakwanisa 4 zvinangwa mu7 kuonekwa mu1999-2000 Coppa Italia uye 1999-2000 UEFA Cup. NaAtalanta, aive nemwaka wakabudirira weligi, achihwina zvibodzwa gumi mumitambo makumi maviri nesere yeSerie A mumwaka wa2000-01. 