Although South Africa has been a democracy for twenty-five years, segregation persists, particularly visible in rapidly expanding urban spaces. This chapter explores the evolution of racial and socio-economic segregation in the South African city. Firstly, a historical overview outlines the initial colonial formation of urban segregation, using the case study of Cape Town to demonstrate how the social and structural form of the city was affected. This is followed by a discussion of the apartheid period, and the legal and socio-spatial dynamics which reinforced segregation of urban population groups. Thirdly, consideration is given to reconstructive post-apartheid urban planning objectives and the intended promotion of inclusive urban development. Finally, post-apartheid planning is explored in the South African interpretation of the neoliberal rationality of developing a globally competitive city. The chapter concludes that the causative dynamics of racial disparity in post-apartheid South Africa reflect a state of perpetual evolution, with socio-economic segregation engrained in the urban landscape.