 Nyorai kuenderera mberi kweiyi ndima - Kaladze akaganhurirwa kumatanhatu chete ekuratidzira uye gumi nematanhatu ekuonekwa mumwaka wa2003-04. Mumwaka unotevera, Kaladze akatamba chete 19 Serie A machisi uye mashanu muChampions League sezvo Milan yakapedza semumhanyi mumakwikwi ese ari maviri. Akanga ari mutsivi asina kushandiswa mumutambo weChampions League mwaka iwoyo, apo Milan yakarasikirwa nepenalty kuLiverpool mushure mekunge 3-3 yakaita. Iye akanzi akaodzwa mwoyo nekushayikwa kwake kwekutanga-timu sarudzo uye kuenda kuChelsea, mukutsinhana naHernán Crespo kana 4 mamirioni, kwakataurwa zvakanyanya. Kaladze pachake akati, Ndakabvumirana zvose nevatungamiri veChelsea. Zvino zvakafanira kumirira kuti vasvike pachibvumirano neMilan uye ndinofunga kuti ndinogona kuva mutambi weChelsea svondo rinouya. Chelsea yakasarudza kusaina Asier del Horno pachinzvimbo. Musi wa30 Chikumi 2005, Kaladze akawedzera kondirakiti yake neMilan kusvika 2010 uye zvakare musi wa4 Gunyana 2006, panguva ino kusvika 2011. Muna 2005-06, kukuvara kwaPaolo Maldini kwakareva kuti Kaladze akaendeswa kumashure kunzvimbo yekudzivirira, chinzvimbo chake chaaifarira. Milan akapedza wechitatu kuti mwaka, kunyange vangadai vakapedza wechipiri kana pakanga pasina 2006 Italian nhabvu tsvina izvo zvakaguma 30 pfungwa deduction. 