Benchmarking techniques are useful and simple tools to analyze the performance of the collective irrigation in the Water User Associations (WUAs) towards an increase in service sustainability. Several benchmarking techniques have been proposed to process and predict performance indicators. Instead, some meaningful statistical techniques based on the distance of data samples, which overcome the limitations of the traditional benchmarking techniques, have never been applied to the collective irrigation sector. This study applies Permutational Multivariate Analysis of Variance (PERMANOVA), Multidimensional Scale Models (MDS), and Distance-Based Linear Models (DISTLM) as benchmarking techniques to evaluate the technical and financial performances of 10 WUAs in Calabria (Southern Italy). These benchmarking techniques revealed that the significant differences in the irrigated areas and financial self-sufficiency of the WUAs, shown by PERMANOVA, depend on the large variability of the remaining performance indicators. Both the MDS and DISTLM demonstrated that a higher number of associated users and larger irrigation service coverage allows an increase in the irrigated areas; this enlargement is facilitated if the water price and the size of the personnel staff decrease. The WUAs’ self-sufficiency is mainly influenced by the number of workers and the maintenance, organization, and management costs, while the impacts of the due service fees and water price are more limited; it is also convenient to increase the number of the associated farmers since this increases the economy of scale and the gross revenues of the irrigation service. Overall, from the analysis carried out for the regional case study, these benchmarking techniques seem to be powerful and easy tools to identify the problems of the irrigation service and help in planning the most suitable policies to improve the sustainability of the collective irrigation at the regional scale.