We compare the role of gender, socioeconomic background and measured ability on students' secondary school placement and professional expectations in Taiwan and the Czech Republic, two countries that have experienced substantial reforms in their educational systems in the context of political change and economic development. Using data from the international PISA 2006 survey of 15-year-olds, our analysis reveals that Czech academic upper-secondary schools are much more selective in terms of socioeconomic background and gender than comparable Taiwanese senior high schools. Controlling for measured ability and other factors, students' professional expectations are also more closely linked to socioeconomic background and gender in the Czech Republic than in Taiwan.