The evolution of urban form is a slow and complex process driven by various factors which influence its pattern of occurrence (time, shape and directions) over time. Given the ever-increasing demand for urban expansion, and its negative effects on travel efficiency and environmental quality, it is imperative to understand the driving forces behind this complex process. This study investigates the role played by transport developments in the expansion of Perth’s urban footprint. Since transport developments are influenced by prevailing economic developments and planning regulations, our analysis starts by deconstructing a timeline of milestones under these three themes, from an urban land development perspective. An overview of the eras of transport evolution is provided, and we discuss the pattern of urban form changes as they relate to these transport advancements. The paper ends by mapping and quantifying changes in Perth’s urban land over the past five decades. The results show that transport had a strong influence on the pattern of urban expansion for a long time, but that trend has now been reversed. Rail constructions have been playing catch-up to residential expansion since the late twentieth century. Meanwhile, the rate of urban expansion has gone down in the twenty-first century, as the city goes for compact growth.