Previous research has shown that parental educational aspirations for their children are an important predictor of children’s academic attainment. However, recent studies have pointed to potential negative effects, in particular if there is a mismatch between parental educational aspirations and the aspirations of their children. This study examines (1) the role of socio-demographic and school achievement–related factors in shaping a potential (mis)match between parental educational aspirations and the aspirations of their children, and (2) whether incongruence between parental and their children’s educational aspirations hinders academic attainment in times of social change. We use data collected for the 1970 British Birth Cohort Study (BCS70) and Next Steps (formerly known as the Longitudinal Study of Young People in England), a cohort of young people born in 1989/90. We find that in both cohorts socio-demographic and achievement-related characteristics are associated with incongruent aspirations, and that incongruent aspirations between parents and their children are associated with a decreased likelihood of participating in and completing higher education. The study contributes to current debates regarding the causes and correlates of discrepancies in educational aspirations and how such discrepancies affect later life chances.