This article investigates the awarding of scholarships to students from historically disadvantaged communities to attend elite schools in South Africa. Specifically, the article analyses the narrated accounts of former scholarship recipients who reflect on their experiences of entering an elite secondary school as scholarship students. Using Bourdieu's notion of cultural capital to explain the interviewees' experiences in the elite school space, the article shows that success in one part of an educational field does not necessarily equate to success in another. Further, providing students with the financial means to access elite education does not mean that they enter into the school contexts as 'equal players'. As such, what the article highlights is that the acceptance of a scholarship for students from historically disadvantaged communities is far more complex and multi-layered than is anticipated by all stakeholders.