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Olive (Olea europaea L.) fruit and derived products play a pivotal role in the Mediterranean diet, to which they contribute their gastronomic value and their health-promoting properties. The fruit cuticle constitutes the interface between the plant and the surrounding environment, and it modulates relevant traits such as water loss, mechanical resistance, and susceptibility to pests and rots. Hence, a better knowledge of fruit cuticle properties and the impact thereupon of agronomic factors could help improving olive grove management. In this work, time–course changes in fruit cuticle yields and composition were assessed during the on-tree ripening of ‘Arbequina’ olives obtained from irrigated or rain-fed trees grown at a commercial grove located in El Soleràs (Catalonia, Spain), where low annual rainfall occur together with cold winters and hot dry summers. Significantly higher wax contents were observed for rain-fed than for irrigated fruits, both in relative (% over total cuticle) and in absolute terms (from 231 to 840 µg cm−2 and from 212 to 560 µg cm−2, respectively, contingent upon the maturity stage), in agreement with their proposed role as a barrier against water loss. Compositional differences in cuticular waxes and in cutin monomers were also detected between irrigated and rain-fed olives, with major changes involving significantly higher loads per surface area of triterpenoids and ω-hydroxy fatty acids in the latter. In contrast to the load and composition of cuticular wax, no apparent impact of irrigation was observed on either total cuticle yields or cuticle thickness. This research was funded by the Plan Nacional de I+D, Ministerio de Ciencia e Innovación (MICINN), Spain, grant number AGL2015-64235-R. C.D. was the recipient of a predoctoral scholarship granted by the Universitat de Lleida.