The present study aimed to analyse the chemical composition and oxidative status of Iberian dry-cured hams from pigs fed different finishing diets: extensive feeding on acorns and pasture in a "Montanera" traditional system (MON), fed in confinement with a mixed diet containing high-oleic sunflower oil (115g/kg of diet) and supplemented with 250mg/kg α-tocopherol (HOVE), and fed in confinement control mixed diet (CON) without added tocopherol and oleic acid fat. Muscles from MON dry-cured hams contained significantly (p<0.05) higher amounts of intramuscular fat (IMF) than those from HOVE and CON hams. The feeding background affected the tocopherol levels in dry-cured hams as those from MON and HOVE pigs had significantly higher levels of α-tocopherol than those from CON pigs whereas the extensive feeding provided muscles from MON pigs with significantly higher levels of γ-tocopherol than the experimental diets did to CON and HOVE pigs. The HOVE diet significantly increased the levels of oleic acid in Iberian dry-cured hams with these levels being similar to the oleic acid levels found in MON hams and significantly higher than those in CON hams. Compared to dry-cured hams from CON pigs, those from MON and HOVE pigs exhibited a higher oxidative stability as a likely result of a most favourable fatty acid composition and the presence of higher tocopherol levels. The principal component analysis (PCA) successfully discriminated between dry-cured hams from pigs fed different finishing diets.