In this paper we investigate how the structure of the educational system, in particular the presence of tracking in secondary schools, is associated with the intergenerational transmission of educational advantage. We study two countries (Italy and Germany) that are both characterized by tracking in secondary schools, although the details of the two systems are rather different in terms of age at tracking, barriers to track entry, and type of credentials generated by school tracks in each country. Research in this area has mainly focused on highest educational attainment of the offspring generation. Apart from that, we emphasize the role of school tracking in analyzing the effects of parental education on subsequent outcomes and transitions within secondary school, as well as the transition to post-secondary education. We ask whether and how the impact of parental education strengthens or weakens in the course of the educational career. To do so, it is important to distinguish between the overall dependencies of educational outcomes on parental education, which are assumed to increase over the life course. On the other hand, controlling for past school performance (grades) and school track, the impact of parental background on certain educational transitions is supposed to weaken at later transitions. In comparing these unconditional and conditional effects of parental education, we aim to identify most sensible educational transitions as well as the impact of (early) tracking within secondary school. Overall our results support the view that parental education is a key factor in sorting students across school tracks, which in turn are important in determining subsequent outcomes. These effects appear stronger in the Italian case than in the German one, and differences between the two educational systems may help understand these findings.