This study examines the transition from surface to drip irrigation in Sector 23 of the Acequia Real del Júcar (ARJ) irrigation district in Spain, through a performance evaluation based on field experiments, on-site observations, and stakeholder perspectives. Spatial observations in 428 plots, representing 51% of the area, revealed that 73% used drip irrigation, 8% used surface irrigation, and 12% was fallow or abandoned. Surface irrigation showed high application efficiency but only met 65.6% of crop water needs, while drip irrigation, with good distribution uniformity, satisfied only 57% and 33.9% of crop needs due to issues such as emitter clogging. Drip systems required higher maintenance (93%) compared to surface systems (14%), which had higher abandonment rates. Main crops cultivated included oranges and persimmons. Herbicide use was common in drip-irrigated fields, while mowing and plowing were more common in surface-irrigated fields. Findings based on farmer and manager perspectives emphasize that, beyond technical efficiency, user behavior and perceptions play a significant role in irrigation system success. These findings provide practical, spatially grounded insights for improving irrigation strategies and irrigation modernization should be evaluated not only in terms of technical efficiency, but also in relation to maintenance requirements, agricultural management practices, and land use decisions. The results can guide policy and investment decisions aimed at enhancing sustainability in agricultural water management.