Abstract: For an urbanised region to be ‘sustainable’, attention needs to be paid to building a transportation network that aligns with sustainable development principles. Such a transportation network should have a minimal ecological footprint, present limited financial burden, and actively promote social cohesion. This study analyses the long term, historical transportation trends of the Gauteng Province of South Africa by comparing four transport studies undertaken between the years 1975 and 2003. Overall, it is demonstrated that adherence to the ‘predict and provide’ transportation planning model has systematically resulted in the enhancement of road infrastructure at the expense of rail, and private transport over public transport. Effective, efficient and low-cost public transport has been systematically under provisioned. Reliance on private vehicles has thus become entrenched and systemic. Consequently, dependence on private vehicles, which was originally confined to the white population (due to apartheid, a racial segregationist policy enforced in South Africa prior to 1994), is now becoming the norm for all race groups. This paper shows how over a century of racial segregation, coupled with spatial apartheid and weak urban transport and land use planning, has resulted in entrenched low-density urban sprawl, a problem further exacerbated by limited mixed land use. Lastly, the study highlights a need for collection of comparable, longitudinal transportation data if long term trends and challenges are to be understood and if successes and failures of policies are to be monitored.