This study showcases the dynamic simulation capabilities of the Urban Biophysical Environments And Technologies Simulator (UrbanBEATS) on a Melbourne catchment. UrbanBEATS simulates the planning, design and implementation of water sensitive urban design (WSUD) infrastructure in urban environments. It considers explicitly the interaction between urban and water infrastructure planning through time. The model generates a large number of realizations of different WSUD interventions and their evolution through time based on a user-defined scenario. UrbanBEATS' dynamics was tested for the first time on a historical case study of Scotchman's Creek catchment and was trained using historical data (e.g. planning documents, narratives, urban development and societal information) to adequately reproduce patterns of uptake of specific WSUD technologies. The trained model was also used to explore the implications of more stringent future water management objectives. Results highlighted the challenges of meeting this legislation and the opportunities that can be created through the mix of multiple spatial scales.