The article presents the retrospective analysis of the territorial organization of the settlement of Kryvyi Rih territory on the basis of a detailed study of topographic maps of various historical periods, namely, the Map of the Polish-Lithuanian Commonwealth, the Special Map of the Western Part of the Russian Empire by F. Schubert, Three-mile military topographic map of the Russian Empire, the Maps of the Office of Military Topographers of the Red Army, the Maps of the German Army, Topo maps of the US Army and Maps of the General Staff of the USSR Armed Forces. The research is based on the authors’ method of retrospective modeling of the historical settlement of the region using historical topographic maps of various time periods and their complex analysis by means of GIS. The results of the research constitute the model of the territorial organization of the settlement process in Kryvyi Rih region. The model represents the historical population resettlement in the studied region and indicates the spatiotemporal changes of the following indexes: the nature and number of settlement locations, the size of settlements, number and density of the population, the ratio of rural and urban populations, etc. The obtained cartographic materials and demographic indicators of resettlement at various times make a significant contribution to the historical and geographical research of the region.