The paper presents a new approach to improving the methods of design and calculation of drainage systems and their technical elements in the drainage mode and in the subsoil moistening mode. This was done on the basis of substantiating the connection of all technical elements of the system and taking into account the influence of their work efficiency on the effectiveness of regulating the water regime of drained lands. The existence and structure of the hierarchical and hydraulic relationship between the parameters of soil flow movement, the parameters of the closed collector drainage network, and the parameters of canals and structures of drainage systems were determined based on the application of the system methodology. A physical model, a structural model, a mathematical model, and a hydraulic model of the drainage system were developed. By using these models, the principles of determining the parameters of the hydraulic characteristics of drainage or water supply (discharge, pressure, velocity etc.) for all elements (drained massif of reclaimed field, collector and drainage network, open canals of the network, main canal, water intake) in the entire range of variation with possible consideration of changes in slopes were obtained. The considered approach will make it possible to evaluate the efficiency of water flow movement simultaneously on every technical element and on the drainage system as their interconnection. In the future, this will make it possible to improve the methods of designing and calculating the technological and structural parameters of drainage systems, and thereby ensure the overall technical, technological, economic, and ecological efficiency of their functioning in accordance with modern conditions and requirements. This is a further improvement of the methods of design and calculation of drainage systems and their technical elements, taking into account the structural, hierarchical, and hydraulic relationship between them in accordance with modern conditions and requirements. This will make it possible to increase the validity and general technical, technological, ecological and economic efficiency of the creation and functioning of drainage systems during the implementation of adaptive measures regarding the changes in climatic conditions and the level of agricultural production in the area of drainage reclamation, for example, in Ukrainian Polissia. It will also provide an opportunity to ensure the necessary level of food security in the region and the country as a whole in the war and post war periods.