Recent technological advances have made possible automated irrigation scheduling using decision-support tools. These tools help farmers to make better decisions in the management of their irrigation system, thus increasing yields while preserving water resources. The aim of this study is to evaluate in a commercial plot an automated irrigation system combined with remote-sensing techniques and soil mapping that allows the establishment of regulated deficit irrigation (RDI) strategies. The study was carried out over 3 years (2015–2017) in a commercial hedgerow olive orchard of the variety ‘Arbequina’ located in Alvarado (Extremadura, Spain). An apparent electrical conductivity (ECa) map and a normalized difference vegetation index (NDVI) map were generated to characterize the spatial variability of the plot and classify the zones in homogeneous areas. Then, reference points were selected to monitor the different irrigation sectors. In 2015, the plot was irrigated according to the farmer’s technical criteria throughout the plot. In 2016 and 2017, two different areas of the plot were irrigated applying an RDI strategy, one under expert supervision and the other automatically. The results show that in a heterogeneous plot the use of new technologies can be useful to establish the ideal location for an automatic irrigation system. Furthermore, automatic irrigation scheduling made it possible to establish an RDI strategy recommended by an expert, resulting in the homogenization of production throughout the plot without the need for human intervention.