Abstract: Water scarcity limits irrigated agriculture, and there is an increasing frequency of situations where farmers must transition from irrigated to dryland cropping systems. This transition poses several challenges, and it is necessary to understand the changes in crop productivity and soil health for the design of viable cropping systems. Our objective was to compare the impact of irrigation retirement on crop production and soil microbial dynamics under the two major crops of the semiarid High Plains. In a formerly irrigated field, we installed a transition experiment that consisted of two irrigation managements, irrigated and non-irrigated (retired), under two cropping systems: continuous maize and continuouswinter wheat. Lower soil moisture after irrigation retirement decreased plant biomass production in both crops, with a higher effect on maize (2 to 6-fold decrease) than on wheat (20% less aboveground biomass production). In both crops, irrigation retirement affected crop development in the order grain yield > aboveground biomass > belowground biomass. Soil microbial communities were less affected by irrigation retirement than the evaluated crops and changes were concentrated in the maize agroecosystem. After three seasons, the high decrease in maize productivity and soil moisture resulted in 50% less extracellular enzyme activity in the dryland treatment, but without consistent effects on microbial biomass or community composition assessed by phospholipid fatty acids. Winter wheat appears as a viable option not only to sustain crop production but also to minimize the negative impacts of irrigation retirement on soil health. However, root production was lower in wheat than in maize, which may affect the long-term evolution of soil organic carbon.