Cities appear to display similar features and mechanisms across different geographies. This phenomenon seems to hold despite planning intentionality. In questioning the nature of this convergent behaviour and the role of path dependence in urban evolution, an attempt is made in this presentation to examine how cities retrieve their relational dependencies between street structures and other formal and functional attributes after the imposition of large scale planning interventions. For the purpose of this investigation, empirical models of historical data are constructed in order to identify the effect of planning on the natural organisation that entwines urban dependencies. The hypothesis is that where planning interventions are more dominant, this natural organisation will be destabilized. The results confirm the hypothesis true for Manhattan and Barcelona. In general, the cases under study are found to share a natural dependency between the network structure of streets, street width, building height and retail land uses. This relationship is thought to characterise the overall trends that cities converge to in the process of urbanisation. An explanatory theory on how cities arrive at this convergent behaviour is thought to be vital for urban design and planning policies.