This article aims to compare two aspects of the education systems in two East European countries. As the political history of the Czech Republic and Poland in the past fifty years is similar, the authors compare the countries' development in tackling educational inequalities and attempt to evaluate their policies and reforms from the beginning of socialism to date. Despite many similarities and identical outcomes in the past (no effect in lowering levels of educational inequalities), these countries undertook two different approaches to the transformation of higher education after 1989. The specific current developments in higher education in the Czech Republic and Poland have been caused by conservative and reserved legislation in the former and the creation of new, very liberal rules for establishing non-state higher education institutions in the latter. As there emerged a considerable difference in the number of higher education institutions in each country, the authors show the negative impact on educational inequalities and the social consequences of the enormous increase in the number of students and private universities. Despite different approaches, the countries face many similar problems, such as quality assurance, a shortage of staff, and information asymmetry. These problems seem to be sharper in Poland, but it is only a matter of time for the Czech Republic.