In this paper, we present the historical time series of enrollment rates in upper secondary schooling in five European countries. The presented data were examined in light of reform attempts aimed at expansions of schooling with the aim to derive lessons for the expansion of the tertiary sector. We were particularly interested in the speed and the differentiation of the expansion. We find that the expansion happened at different speed. It took 9 to 26 years for a country to massify its upper secondary education and further 11 to 41 years to universalize it, with gross enrollment rates reaching 80%. The expansion was slower in the leaders of expansion, such as the United Kingdom or Sweden. In contrast, laggards were able to catch up relatively fast, once the limiting conditions of expansion were removed. Although there has been a general trend towards expansion of the general upper secondary education, the popularity of vocational tracks has been diverse across examined countries.