Urban development causes multiple water losses. Some of them may be ignored but some could have a huge influence on the whole catchment, including soil drought. As urban sprawl rises, space for unaffected infiltration and retention is increasingly limited. The objective of this study was to backcast and to estimate water-retention loss due to urbanization during the period of 1990–2018. We used landcover data, meteorological and hydrological data and data on soil water-holding capacity. Water-retention loss was expressed as soil water retention capacity loss, net precipitation loss and total sum of precipitation loss. Historical change in urban extension has led to large impacts on the hydrological cycle of the study area. Progressive urban development caused water-retention losses which range from 3.380 to 14.182 millions of cubic meters—depending on the methodology used. Hydrological analysis showed the lack of a significant trend (decrease trend) of low flow which is caused by the high percentage of natural land use in the upper part of catchment. Our results show that backcasting of water retention change using CLC data (a) brings new and plausible data on retention loss, (b) is possible to replicate and (c) data used are common and easy-to-get.