For underpasses in Yeongjong Sky City business district, the guided drainage system, as a buoyancy prevention system has been designed, and is under construction. This paper investigates the safety of the guided drainage system for underpass structures being constructed in Yeongjong Sky City business district. This paper also calculates the amount of outflowing groundwater generated by the guided drainage system, and proposes alternative usages of the water. In order to investigate safety and field applicability of the guided drainage system for underpasses, characteristics of the surface flow for the area of interest have been analyzed, and the flow change of groundwater following the underpass structure construction has been evaluated using the 3-dimensional groundwater program MODFLOW. The influence of ground water on safety of the underpass structures has been calculated by FLAC2D analysis. For alternative usages for the outflowing groundwater generated by the guided drainage system, utilization methods of the outflowing groundwater in national and international resources have been researched. The amount of an outflowing groundwater to be generated in the area of interest has been analyzed, and efficient potential usages of this groundwater have been researched. When guided drainage technique is applied, the change in flow of groundwater must be evaluated and considered as safety factor relating to the buoyancy of the structure. As a result, safety factor demonstrated more than 1.2, meaning that the underpass structure is safe. The amount of subsoil drain generated by the guided drainage system was also analyzed. The quality and amount of water satisfied the standards and volume requirements, so as to make it applicable for a number of uses, such as X, Y, and Z, and should prove to be a valuable resource as the circumstances of the neighboring area change over time. These resources can be used as basic data for future urban water circulation studies, as well as generating research of alternative water usages.