Although communist ideology claimed to destroy former class stratification based on labour market capitalist relationships, "de facto" during socialism one social class hierarchy was substituted for another that was equally unequal. The economic transition during the 1990s increased stratification by wealth, which affected educational inequality. This study examines the relationships among parental education, gender, educational expectations and mathematics achievement of youths in five post-socialist Eastern European countries, comparing them with three Western countries. We employed the 8th-grade data from the Trends in International Mathematics and Science Study (TIMSS) 1995 and 2007. The findings point to the universal associations between parental education and student outcomes, whereas gender comparisons present interesting East-West differences. The theoretical and policy implications of these findings are discussed.