 Kunyora kuenderera kweiyi ndima - Mushure mekuve nhengo yechikwata chevechidiki cheEmpoli kubvira 1994, Di Natale akatanga basa rake rehunyanzvi nechikwata chevakuru cheEmpoli muna 1996, uye akaramba ari mukirabhu kusvika 2004, kunze kwekupfupisa kwechikwereti neIperzola, Varese uye Viareggio. Munguva yake neEmpoli, akabatsira kirabhu kuwana kukwidziridzwa kuSerie A mumwaka wa2001-02 Serie B, achihwina zvibodzwa gumi nezvitanhatu. Kubudirira kwake kwakauya panguva ye2002-03 Serie AMwaka, sezvo akarova zvibodzwa gumi nematatu muligi uye akabatsira Empoli kudzivirira kudzikiswa. Pasinei nekusakwanisa kuwana mambure nguva dzose kana kuchengetedza Empoli kubva pakudzingwa mumwaka unotevera, maitiro ake uye zvinangwa zvinogadzikana zvakamuita kuti aende kuUdinese mu2004. 