This paper introduces issues of agricultural drainage systems from the views of former, current, and future roles and the functioning of these systems in Central Europe. A methodologically disparate survey was done on 39 model locations in the Czech Republic with different intensities and states of land drainage systems, aimed at describing commonly occurring problems and possible adaptations of agricultural drainage as perceived by farmers, land owners, and landscape managers, or by protective water management. The survey was focused on the technical state of the systems, fragmentation of land ownership within drained areas, and on possible conflicts between agricultural and environmental interests in a landscape. Achieved results confirmed that there is obviously an increasing need to reassess some functions of prevailingly single-purpose agricultural drainage systems. Drainage intensity and the detected unfavourable technical state of drainage systems as well as the risks connected with the anticipated climate change from the view of possible water scarcity claims for a complex solution. An array of adaptation options for agricultural drainage systems is presented, aimed at enhancement of water retention time and improvement of water quality. It encompasses additional flow-controlling measures on tiles or ditches, or facilities for making selected parts of a drainage system inoperable in order to retain or slow down drainage runoff. However, it was revealed that the question of landowner parcels fragmentation on drained land would dramatically complicate the design and realization of these measures. Presented solutions and findings are propounded with respect to contemporary and future state policies and international strategies for sustainable agriculture, water management, and the environment.