Adaptation to climate change is a major challenge facing the agricultural sector worldwide. Olive (Olea europaea L.) is a global, high value crop currently cultivated in 28 countries worldwide. Global data to assess the vulnerability of the crop to climate variability are scarce, and in some notable cases, such the United Nations Food and Agricutlure Organization database (FAO, 2006), qualitative assessments rather than quantitative indicators are provided. The aim of this study is to demonstrate a new approach to help overcome these constraints toward a globally applicable method to assess the adaptability of olive cultivars. The adaptability of 11 cultivars, widely used in 11 countries worldwide, was studied using a new generic approach based on the evaluation of soil hydrological regime against cultivar-specific hydrological requirements. The approach requires local data, notably on soil hydrological properties, but it is easily transferable to other countries and regions. We applied an agrohydrological model in 60 soil units to determine hydrological indicators both in a reference (1961–1990) and a future (2021–2050) climate case. We compared indicators with cultivar-specific requirements to achieve the target yield; requirements were established using experimental yield response curves. We estimated the probability of adaptation, i.e., the probability that a given cultivar attains the target yield, and we used it to evaluate the cultivar potential distribution in the study area. At the locations where soil hydrological conditions were favorable, the probabilities of adaptation of the cultivars were high in both climate cases. The results show that the area with suitable conditions for the target yield (area of adaptability) decreased under future climate for all the cultivars, with higher reduction for Frantoio and Maiatica and smaller reduction for Itrana, Nocellara, Ascolana, and Kalamata. These cultivars are currently grown in Argentina, United States (US), Australia, France, Greece, and Italy. Our results indicate also that these cultivars require higher available soil water to attain the target yield, i.e., we may expect similar vulnerability in other parts of the world. Based on these findings, we provide some specific recommendations for enrichment of global databases and for further developments of our approach, to increase its potential for global application.