In this article, a comparison is drawn between the demographic characteristics of these two Slavonian-Srijem towns during the period of their moulding into urban entities at the end of the 18th century and beginning of the 19th. The author applies the comparative approach and endeavours to establish the similarities and differences between Vinkovci and Vukovar in the demographic structure and forms of settlement of those two centres during their »initial urbanisation«. Starting out from the justification for comparison of these two towns – their spatial proximity, similar historical circumstances, the comparable eco-historical systems that gave rise to them, as well as their diverse status within the Hapsburg Monarchy – when comparing them, the author sees the great influence of the State and absolutist reforms on urban development in those border settlements in the Croatian and Hapsburg region. Apart from that, the demographic aspect and the role of migration, along with the organised settlement policy, was of great importance in their urban moulding. The needs of Vinkovci and Vukovar as urban centres with new inhabitants were largely covered by moving in people from other parts of the Monarchy, and also from the Croatian lands under other jurisdictions and other countries under Ottoman authority. Bringing in new inhabitants from various regions enabled the recovery and strengthening of those settlements after the Ottoman era. Despite the influx of new demographic elements, the entire region of Slavonia and Srijem – as was the case with Vinkovci and Vukovar – represented a poorly inhabited area in comparison with other parts of the Monarchy. An important role in the life of those towns was played by the largest ethnic and/or religious groups, the Roman Catholic and the Christian Orthodox believers.