Calabria (southern Italy) is a flood prone region, due to both its rough orography and fast hydrologic response of most watersheds. During the rainy season, intense rain affects the region, triggering floods and mass movements that cause economic damage and fatalities. This work presents a methodological approach to perform the comparative analysis of two events affecting the same area at a distance of 15 years, by collecting all the qualitative and quantitative features useful to describe both rain and damage. The aim is to understand if similar meteorological events affecting the same area can have different outcomes in terms of damage. The first event occurred between 8 and 10 September 2000, damaged 109 out of 409 municipalities of the region and killed 13 people in a campsite due to a flood. The second event, which occurred between 30 October and 1 November 2015, damaged 79 municipalities, and killed a man due to a flood. The comparative analysis highlights that, despite the exceptionality of triggering daily rain was higher in the 2015 event, the damage caused by the 2000 event to both infrastructures and belongings was higher, and it was strongly increased due to the 13 flood victims. We concluded that, in the 2015 event, the management of pre-event phases, with the issuing of meteorological alert, and the emergency management, with the preventive evacuation of people in hazardous situations due to landslides or floods, contributed to reduce the number of victims.