In this article, we aim to explain the school careers of the second generation of Turkish immigrants in nine cities in five Western European countries and show the influence of the national school systems ranging from comprehensive to hierarchical tracking structures. We apply sequence analyses, optimal matching, and cluster analyses to define school trajectories complemented with propensity score matching to study the differences between young adults of different origin. Participants were 4516 young adults of Turkish second generation and native origin aged between 18 and 35. Findings show that the school system makes a difference for school careers: (1) in rigid systems with higher differentiation and early tracking, the gap between the second-generation and native school trajectories begins to unfold early in the school career; (2) in the rigid systems, the track in which students enter secondary education determine the routes they take as well as their final outcomes; and (3) more open systems allow for “second-chance” opportunities for immigrant students to improve their track placement. However, across school systems, second-generation youth follow more often non-academic or short school careers, while native youth follow academic careers. When individual and family background are controlled via propensity score matching, the ethnic gap is explained better in more stratified systems highlighting the important role of family background in more stratified school systems.