In the Mediterranean region, crop productivity and food security are closely linked to the adaptation of cropping systems to multiple abiotic stresses. Limited and unpredictable rainfall and low soil fertility have reduced agricultural productivity and environmental sustainability. For this reason, crop management technologies have been developed, with a special focus on the Mediterranean region, to enhance crop production by increasing land productivity and sustaining soil fertility under influence of climate changes and population increases. The main objective of this study was to analyse dryland Mediterranean cropping systems, and to discuss and recommend sustainable cropping technologies that could be used at the small-scale farm level. Four crop management practices were evaluated: crop rotations, reduced tillage, use of organic manure, and supplemental and deficit irrigation. Among the tested interventions, incorporation of crop residues coupled with supplementary irrigation showed a significantly positive effect on crop productivity, yield stability and environmental sustainability.