Sterol composition was studied for three successive crop seasons in some olive oils extracted from Italian cultivars grown in Reggio Calabria Province, Southern Italy. Three autochthonous cultivars from Calabria Region: Cassanese, Ottobratica, and Sinopolese and seven allochthonous cultivars: Coratina, Itrana, Leccino, Nocellara Messinese, Nociara, Pendolino, and Picholine were investigated. The studied olive oils showed an acceptable sterol composition in accordance with either the European Union or International Olive Oil Council regulations. The Picholine cultivar showed the highest content of total sterol, β-sitosterol, chlerosterol, campesterol, and of cholesterol. The contents of Δ 5 -avenasterol, Δ 5,24 -stigmastadienol, 24-methylene-cholesterol, and Δ 7 -avenasterol were high in Nociara cultivar, whereas Pendolino cultivar had the highest content of sitostanol and Sinopolese cultivar gave the highest content of stigmasterol. Results confirmed the existing significant differences (P < 0.05 and P < 0.01) in the cultivar, crop season, and crop season × cultivar.