Facing substantial challenges due to rapid urbanization and socio-political shifts, the urban identities of our cities are in a state of significant transformation. This study explored the dynamic evolution of Damascus’s urban identity over distinct historical periods, employing a multi-dimensional methodology, which integrated spatial assessments, observational data from urban planners, and historical analyses. The findings revealed a transition from a stable urban identity in the pre-colonial period, to fragmented and, eventually, lost states in the post-colonial era. This study has underscored the need for strategic interventions to preserve the city’s identity amidst modernization pressures, providing valuable insights for urban planners and policymakers. The findings underscore the pressing need for strategic, context-sensitive interventions that can restore and revitalize Damascus’s unique urban identity, contributing to a broader discourse on the sustainable preservation of the cultural heritage in historic cities facing modernization pressures.