The paper reports on research on the transformation of the relationship between higher education and the world of work after 1989, using Bulgaria as a case study. The literature suggests that in order to analyze transformation in Bulgaria, we need to explain what this relationship was like prior to 1989, when admission policies played a key role partly, because graduates were centrally distributed to jobs after their graduation. The paper focuses on the aspect of access to higher education. It explores how inequalities in access have been changing over time, using an ’inequality index’. The capability approach is applied in the analysis of these changes, having in mind that it provides a framework in which to conceptualize, measure and evaluate such phenomena as inequalities, poverty and well-being. The paper argues that, although the expansion of higher education in Bulgaria before and especially after 1989 enhances both ’process’ and ‘opportunity’ freedoms of students to be educated in higher education institutions, it does not go hand in hand with reducing inequalities to access higher education. Data from the European Social Survey will be used to show how we can look at this problem in both historical and comparative perspective.