This article presents a comparative analysis of educational inequality by family background and gender in Taiwan and the Czech Republic, which have both experienced substantial educational expansion in the last half-century under different educational systems. We highlight the specific institutional histories of both countries and examine the role of dead-end tracks in mediating educational inequality by family background. Pooling the most recent data available, we use probit analyses of inequality in secondary and tertiary educational attainment across 5-year birth cohorts from 1956 to 1985. In terms of secondary educational attainment, we find that the gap in inequalities by family background between the countries is large, with a decline in inequality in Taiwan but persistent inequality in the Czech case. We attribute these findings to differences in educational expansion and characteristics of the secondary school system. However, in tertiary educational attainment, we find similarities in educational inequality between the two countries.