This paper examines educational inequality in the city of Melbourne, Australia, as part of the International Study of City Youth (ISCY). The paper takes two schools participating in ISCY, which contrast in ways that illustrate important aspects of inequality in the Melbourne education system. It begins by outlining the policy context of school choice and competition currently dominant in Australia, and examines how performance and accountability measures position these two schools as a ‘winner’ and a ‘battler’ in the education marketplace. It then uses baseline data from the ISCY project to explore the differences between the schools more deeply, and reveal how the ‘enterprise culture’ interacts with the characteristics of schools and students to exacerbate educational inequality.