This study explores how patterns of institutional differentiation in higher education systems are linked to educational inequalities at the transition from higher education to work. We measure institutional differentiation within countries along two dimensions: degree level that mainly structures educational inequalities in occupational status attainment, and occupational specificity that mainly structures educational inequalities in labour market entry dynamics. We argue that convergence processes have lead to similar patterns of institutional differentiation in higher education across the five post-socialist Central- and Eastern European countries studied here. Educational inequalities at the transition from higher education to work should, therefore, also follow similar patterns across countries. Our empirical results show that degree level is a central determinant of occupational status in respondents’ first job, with university master graduates reaching the highest occupational positions, followed by university bachelor and vocational college graduates. In terms of labour market entry dynamics, the slowest transitions into first employment are observed among graduates from least occupation-specific programmes, but overall the relationship between occupational specificity and labour market entry dynamics is more complex. Altogether, we find considerable similarities across countries in patterns of institutional differentiation and educational inequalities at the transition from higher education to work.