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The aim of this study is to evaluate the physical, nutritional, and sensory properties of cheese obtained from goats fed a dietary supplementation with olive leaves (OL). Thirty Saanen goats were randomly allocated into two groups of 15 goats each, (1) a control group fed with a standard diet (CG), and (2) an experimental group (EG) fed an OL-enriched diet. The trial lasted for 30 days. The milk of each group was then collected and used to produce Caciotta cheese, which was analyzed at the beginning and at the end of the ripening period (60 days). The results showed a positive effect of dietary OL supplementation in improving the fatty acid profiles due to the significant increase of unsaturated fatty acids, mostly α-linolenic acid (C18:3 n-3), with the consequent reduction of the ω-6/ω-3 ratio, a condition commonly associated with an increased health functionality of food products. Moreover, improved oxidative stability was observed in cheese during ripening, a presumable consequence of the transfer into the milk of dietary bioactive compounds, mainly polyphenols of high biological value, and credited as a marked antioxidant potential. Furthermore, reduced lipolytic action was observed in 60-day ripened cheese, even if no significant changes in sensory properties were evidenced.