Flash floods have been the cause of some of the most devastating events worldwide. The wide diversity of the effects, as well as the variety in the severity of the impacts, lead to major obstacles in obtaining a realistic understanding of the damages caused by a flood event, thus hampering at the same time our ability to predict future impacts. In assessing flood impacts and their severity, most existing methods use a qualitative characterization (e.g., major, catastrophic, etc.) or view the impacts from a single viewpoint or discipline (e.g., economic losses). In this study, we apply the Flash Flood Impact Severity Scale (FFISS) to assess, map, and classify the impacts of two flash floods from the Lilas River in Greece in 2009 and 2020. This application aims to discuss the different severity levels in terms of how one flood can affect the impacts of the next event. The methodology encompasses comprehensive field research, including the collection of ground-based and aerial observations utilizing UAV technology to document the impacts. These observations are subsequently georeferenced, followed by application of the Flash Flood Impact Severity Scale (FFISS) and generation of detailed maps to assess and evaluate the severity of the impacts associated with the two flood events. The results show that despite the higher water stage of the second flood, the impacts in previously hit areas indicate lower severity values, attributed to the gradual adaptation of the community and its infrastructure, as well as significant local widening of the river channel. On the contrary, high severity remains an issue in newly flooded areas during the second event. Overall, the application of the FFISS can show the spatial patterns of severity impacts, providing insights into the nature of floods locally but also indicating a potential reduction in the overall risk in the post-flood period.