Zadar and Šibenik are two largest cities in northern Dalmatia with rich historical, cultural and economic traditions and long continuity of urban development. As with other Croatian cities, throughout the history their urban development has been very slow and intermittent until the second half of the 20th century, when, through the process of urban-based industrialization, they recorded accelerated trends in the development and transformation of their spatial structure while also affecting and transforming their surroundings and region. However, partly as a result of predetermined and partly spontaneous developmental assumptions, Zadar has to this day developed into the 5th most populous city in Croatia and an important fast-growing regional center with large gravitational area, while Šibenik substantially lagged behind Zadar and in some segments even declined compared to development state it achieved in period before the Homeland War. Therefore, this paper closely analyzes and compares the major urban development trends of these two cities with particular emphasis on the post- World War II period. In doing so, it points out main similarities and differences in their urban development, as well as the factors that enabled Zadar to reach a higher level of development than Šibenik.