This study focuses on topographic hollows, their flow direction and flow accumulation characteristics, and highlights discharge of hillslope seepage so as to understand porewater pressure development phenomena in relation with slope failure in topographic hollows. For this purpose, a small catchment in Niihama city of Shikoku Island in western Japan, with a record of seven slope failures triggered by typhoon-caused heavy rainfall on 19?20 October 2004, was selected. After extensive fieldwork and computation of hydro-mechanical parameters in unsaturated and saturated conditions through a series of laboratory experiments, seepage and slope stability modellings of these slope failures were done in GeoStudio environment using the precipitation data of 19?20 October 2004. The results of seepage modelling showed that the porewater pressure was rapid transient in silty sand, and the maximum porewater pressure measured in an area close to the base of topographic hollows was found to be higher with bigger topographic hollows. Furthermore, a threshold relationship between the topographic hollow area and maximum porewater pressure in this study indicates that a topographic hollow of 1000 sq. m area can develop maximum porewater pressure of 1.253 kPa. However, the porewater pressures required to initiate slope instability in the upper part of the topographic hollows is relatively smaller than those in the lower part of the topographic hollows.