Using all available waves of the Trends in International Mathematics and Science Study (TIMSS) from 1995 to 2011, this study examines the factors influencing educational expectations of students in five Eastern European countries (Hungary, Lithuania, the Russian Federation, Romania, and Slovenia). We consistently find across countries and waves that parental completion of a college degree, better material well-being of the family, and being a female are positively associated with students’ expectations to complete college. Furthermore, we find that students who come from more advantaged families are more likely to have formed their academic plans by the eighth grade compared to their disadvantaged peers.