Over the last 150 years, and particularly after WWII, comprehensive spatial masterplans, aimed at increasing efficiency, amenity, and value of degraded urban neighbourhoods, were developed all over the UK. However, contrary to the implicit assumption of their creators that stable long-term outcomes could be planned and achieved, resulting environments often failed to demonstrate the resilience necessary to deal with the multi-scale changes cities constantly face throughout their existence, often worsening the problems they set out to solve. Masterplans were hence object of strong criticism and only very recently, guided by new place-making principles, they started to be re-evaluated. Yet, are today’s masterplans shaping places any better equipped to respond to the pace of current urban change? How can masterplans help making places better suited to positively respond to changes over time? To answer these questions, we explore the concept of resilience in comparing examples of pre-Industrial, post-WWII and contemporary masterplans. We present a longitudinal study that looks at the Gorbals district of Glasgow over time as it undergoes three emblematic masterplanned redevelopments, and observe them against the five resilience proxies of diversity, redundancy, modularity, connectivity and efficiency. Results suggest that the transition from the 19th century original development to the post-WWII modernist redevelopment produced a remarkable drop in overall place resilience, only partially recovered by the recent multi-agency mixed-use redevelopment.