The expected increase in precipitation and temperature in Scandinavia, and especially short-time heavy precipitation, will increase the frequency of flooding. Urban areas are the most vulnerable, and specifically, the road infrastructure. The accumulation of large volumes of water and sediments on road-stream intersections gets severe consequences for the road drainage structures. This study integrates the spatial and temporal soil moisture properties into the research about flood prediction methods by a case study of two areas in Sweden, Vastra Gotaland and Varmland, which was affected by severe flooding in August 2014. Soil moisture data are derived from remote-sensing techniques, with a focus on the soil moisture-specific satellites ASCAT and SMOS. Furthermore, several physical catchments descriptors (PCDs) are analyzed and the result shows that larger slopes and drainage density, in general, mean a higher risk of flooding. The precipitation is the same; however, it can be concluded that more precipitation in most cases gives higher soil moisture values. The lack, or the dimensioning, of road drainage structures seems to have a large impact on the flood risk as more sediment and water can be accumulated at the road-stream intersection. The results show that the method implementing soil moisture satellite data is promising for improving the reliability of flooding.