The stormwater drainage problem is one of the major challenges facing in Shire Endaslasse town, Ethiopia. In a town, Street flooding and overtopping drainage system problems are occurring during the rainy season. This causes ponding which poses difficulties in ease of transportation and it hinders the day-to-day activity of the people. So, the study focuses on the performance of the stormwater drainage system in Shire Endaslasse town using Arc GIS and SWMM5.1. For this study, the primary data were collected by field surveys and interviews with the council body. Simulation results for storm events show that in some of the drainage systems in different regions of Shire Endaslasse town have flooded. During the field observation, the drainage structures are filled with solid wastes, inadequate inlet and outlet structures and some of the top element of the manhole have been broken this may cause a problem of aesthetic and healthy at large it may increase flood risk. The flooding risk in the drainage systems is very high due to the drainage system is undersized to cope with the current rainfall rates, but also is very limited to face the upcoming predicted rainfall.