Kammala jumla mai zuwa: Bayan jan hankalin sha'awar Inter Milan, a tsakiyar 1979, Ancelotti ya koma Roma, kuma ya fara buga wasan Serie A a wasan da suka yi da AC Milan a ranar 16 ga Satumba. A karkashin kocin Nils Liedholm, an tura shi a matsayin dan wasan tsakiya ko kuma dan wasan tsakiya kuma ya zama daya daga cikin 'yan wasan da suka fi muhimmanci a kulob din a cikin tawagar da ta hada da' yan wasan Brazil Falcão da Toninho Cerezo, da kuma 'yan wasan kwallon kafa na Italiya Roberto Pruzzo, Bruno Conti, Agostino Di Bartolomei, da Pietro Vierchowod, nan da nan suka lashe gasar Coppa Italia a jere a farkon shekaru biyu tare da kulob din. A lokacin shekarunsa takwas a kulob din, ya lashe Coppa Italia sau hudu (1980, 1981, 1984, da 1986). Bayan fama da raunin gwiwa, da kuma gudanar da matsayi na biyu da na uku a gasar a
1981 da 1982, Ancelotti ya taimaka ya jagoranci tawagar don lashe gasar zakarun Italiya ta tarihi a 1983, taken gasar ta biyu a tarihin kungiyar. A kakar wasa ta gaba, har ma ya taimaka wa Roma ta sake lashe kofin Coppa Italia kuma ta kai wasan karshe na Kofin Zakarun Turai a shekarar 1984, kodayake ta rasa wasan karshe saboda rauni yayin da Liverpool ta doke Roma a bugun fanareti a Stadio Olimpico a Rome. An nada shi kyaftin din kungiyar a shekarar 1985 a karkashin sabon manajan kulob din Sven-Göran Eriksson, kuma ya zama jagora ga matashin dan wasan tsakiya Giuseppe Giannini, yayin da Roma ta lashe Coppa Italia, amma kuma ta sake rasa taken gasar a lokacin gasar 1985-86 Serie A, inda ta kammala a matsayi na biyu a bayan Juventus.