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The study of urban transport service systems covers a wide range of issues connected with sustainability of urban areas, provision of high quality services and administrations in the cities and urban agglomerations that have transport problems related to population mobility. Each city develops its own particular concept of the transport service system development, based on a variety of external and internal factors. The article deals with transport development policies of two cities - Moscow and Colombo completely different in almost every aspect such as history, geopolitics etc, except one: both are the biggest capital cities of the Corresponding states, Russian Federation and Sri Lanka. The task of the authors was to make theoretical comparative analysis of the most significant tendencies, processes and effects in the field of modern urban transport development of the above mentioned cities in order to identify their context specifics and factors that could determine the relationships between the development of the settlement system and the level of development of the transport system that allow to dialogue enrichment in strategic planning and practical decisions. The article presents the methods of analysis, statistical data, the results of a retrospective analysis of the relationship between the historical process, the modern management system and the level of development of urban transport service systems.