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In this study, we analyzed how secondary school tracking relates to students’ self-beliefs (i.e., their academic self-concepts in different domains and their beliefs regarding their labor market chances) and school disengagement during a time period that has received little attention in educational psychological research on tracking: when students are at the end of schooling and on the verge of entering the labor market. In doing so, we disentangled 2 distinguishing features of tracking: tracks as social contexts (operationalized via track level and the mean achievement of students’ schoolmates) and tracks as pathways to different future opportunities (operationalized via educational certificates). Using questionnaire, achievement, and administrative school data from 2,155 students from 29 low-track schools, 23 intermediate-track schools, and 35 comprehensive schools in Berlin, Germany, we found educational certificates to be the most important factor shaping students’ self-beliefs and school disengagement. Irrespective of their individual achievement, their schoolmates’ achievement, and their track level, students who received the intermediate school-leaving certificate had higher academic self-concepts, believed that their certificate would give them better chances of success in the labor market, and were less disengaged from school than students who received the low school-leaving certificate. In contrast, students’ track level did not serve as a predictor for the outcomes considered. The achievement of students’ schoolmates (i.e., the big-fish-little-pond effect) was only relevant for students’ academic self-concepts and not for students’ self-beliefs regarding labor market entry or their school disengagement.