 Nyorai kuenderera mberi kweiyi ndima - Muna Kukadzi 1999, Ancelotti akagadzwa kuve maneja weJuventus, kwaakabudirira uye akatungamira Marcello Lippi, uyo akadzokera kukirabhu apo Ancelotti akasiya. NaJuventus, Ancelotti akazova asinganetsi nekugadzirwa kwechikwata, achisiya 442 yake yaaifarira kuitira kuti agone nyeredzi yeFrance playmaker Zinedine Zidane mune yake yaanofarira yemahara basa kumashure kwevanotungamira muchikwata chekutanga. Mwaka wake wekutanga wakazara kuJuventus wakatanga kuvimbisa, sezvo akabva atora mukombe weIntertoto nekirabhu nekurova Rennes 42 pahuwandu, kunyangwe Juventus yakatambura kutenderera kwe16 kubviswa muEFAFA Cup, uye yakarasikirwa nemutambo weligi kuLazio nepfungwa imwe chete pazuva rekupedzisira remutambo wemwaka; izvi zvaive mushure mekurega kutungamira kwemapoinzi mashanu nemitambo mitatu yasara, iyo yakakwezva kushoropodzwa kwakasimba kubva kuvateveri uye bhodhi revatungamiriri. Mwaka wakatevera, Ancelotti akaenda asina mukombe, achipedza ari wechipiri muSerie Azvakare, kuRoma, uye akadzingwa neJuventus. Ancelottis dismissal was announced by Juventus at halftime in the final league game of the season at home against Atalanta, on 17 June 2001, even though they were still within a chance of winning the title; Juventus yakakunda mutambo 21, kunyange zvazvo mhedzisiro yacho yakanga isina kukwana kuvadzivirira kubva pakupedzisa kumashure kweRoma muligi. Ancelotti akapedza basa rake neJuventus aine rekodhi yemakumi matanhatu nematanhatu ekukunda, makumi matatu nematatu uye 18 kurasikirwa. 