Trees have the ability to respond to local environmental cues by expressing particular phenotypes across their canopy through a mechanism known as intracanopy plasticity. In this study, intracanopy plasticity of Olea europaea subsp. europaea was analyzed by sampling leeward and windward canopy exposures of individuals occurring in an area with sustained strong wind conditions. A suite of morphofunctional and reproductive traits was measured at these contrasting canopy positions and, for comparison, also in wind-protected trees. Furthermore, the pattern of intracanopy plasticity of these plants was compared to that previously documented in a closely related species, Olea europaea subsp. guanchica. Plants exposed to strong winds displayed substantial differences between leeward and windward exposures in most of the study traits. Leeward exposures experienced a mean reduction of 73% in wind speed as compared to windward ones, and displayed a modular phenotype matching that observed in wind-protected plants. Wind-exposed plants, however, were comparatively smaller and had fewer and smaller inflorescences, since inflorescence size was positively associated with crown size. The two closely related species showed similar crown and leaf sizes between populations exposed to strong winds, and intracanopy responses were comparable for most traits. These observations suggest that intracanopy plasticity resulted in the expression of contrasting phenotypes within individuals, which allowed trees to persist under sustained wind stress, although at the cost of a reduced reproductive fitness. In addition, this study gives support to the idea that intracanopy responses are conserved among closely related taxa evolving in different habitats, but experiencing a comparable limiting factor.