In this paper, we examine the intersections of childbearing and educational attainment in urban South Africa. We compare the pathways of adolescent fertility according to race and how they impact educational attainment. Although racial apartheid ended, our preliminary results show that today’s adolescents experience different pathways to adulthood associated with race. Different childbearing experiences may lead to very different educational careers. Insufficient panel data in developing countries has hindered studies examining childbearing and schooling. We use data from the Cape Area Panel Study, a panel of 4,800 young people in Cape Town, to answer: How do adolescents experience childbearing in post-Apartheid South Africa? How do these pathways drive adolescents’ educational attainment for different racial groups? For adolescents enrolled in school in Wave 1, we examine the factors leading to a birth between waves. We then look at the factors driving educational attainment after birth, including test scores implemented in Wave 1.