While it is well established that the structure and organization of the education system affects youth transitions, less attention has been paid to the study of qualitative distinctions at the same level of education over time in the Irish context. Using data from the School Leavers’ Survey over the period 1980-2006, this paper considers the hypothesis of effectively maintained inequality in the case of the Republic of Ireland. The data capture young people’s transitions during three distinct and remarkable macro-economic fluctuations, and makes a particularly interesting test case for EMI. Over the cohorts under investigation, Ireland had changed from a recessionary economic climate and prolonged economic stagnation for much of the 1980s to a booming economy by the middle of the mid-2000s and one of the most dynamic economies in the world during the “Celtic Tiger” period. The patterns of social-class inequality over a 30-year paper reported in this article suggest that qualitative differences at the same level of inequality represent a persistent barrier to greater equality in the Irish context. Specifically, we find three notable patterns to support the hypothesis of EMI with regard to tracking decisions taken in the transition from lower secondary to upper secondary, subject-level differentiation in the upper secondary mathematics curriculum, and access to university higher education.