Population growth, increasing demands for food, ever-growing competition for water, reduced supply reliability, climate change and climate uncertainty and droughts, decline in critical ecosystems services, competition for land use, changing regulatory environments, and less participatory water resources governance are contributing to increasing difficulties and challenges in water resource management for agriculture and food. The need for sustainable food security for our global population and the need for preserving the environment, namely natural and man-made ecosystems and landscapes, have created an increased need for integrated, participative and scalable solutions focusing the various levels of irrigation and nature water management, from the field crop to the catchment and basin scales. Meanwhile, challenges and issues relative to water management for agriculture and food have evolved enormously in the last 30 years and the role of active management of the components of the water cycle is assuming an increased importance since their dynamics are key to assure water use sustainability, mainly agriculture and natural ecosystems sustainability. However, different regions face context-specific challenges associated with water scarcity, climate, governance, and population requirements. The main and first challenge is producing enough food for a growing population, which is intimately related with challenges placed to agricultural water management, mainly irrigation management. This paper revises challenges and progress achieved in the last 30 years focusing on irrigated agriculture, mainly water management, and its contribution to food security and the welfare of rural communities.