On October 24, 2014, a severe flood event took place in the entire Athens basin with extensive damages due to a short-duration rainfall event of high intensity. This work focuses on the analysis of the characteristics of this specific flood event by investigating the influence of various factors on the spatial distribution of urban flooding. Factors that are linked to flood occurrence are either static, linked to the surface and structure characteristics (i.e., the terrain slope, the buildings’ lower opening level, etc.), or dynamic, such as the rainfall depth and intensities for various durations. All factors’ values are determined with the use of GIS techniques and finally logistic regression is used to evaluate their statistical correlation with flood occurrence. Results illustrate that a number of factors appear to influence the distribution of flood incidents in an urban environment to a certain degree.