Middle schools are important because they launch students on trajectories that they are likely to follow throughout their formal educations. This study explored the relationship of first-generation segregation (elementary and middle school racial composition) and second-generation segregation (racially correlated academic tracks) to reading and mathematics test scores of Grade 8 students who attended the Charlotte-Mecklenburg Schools (CMS) in 1997. At the time the data were collected, the district had been operating under a mandatory desegregation plan since the early 1970s, which it continued to do for another five years. While the majority of students attended desegregated schools for most of their CMS education, a portion of youth also experienced school- and classroom-level segregation. Survey data collected from 1,812 students in randomly selected language arts classes stratified by track from the district's 24 middle schools were analyzed with multilevel modeling to examine the influence of school and classroom racial composition on standardized scores, controlling for student and family factors associated with school performance. Results indicate that school- and classroom-level racial segregation was negatively related to achievement. Beginning in elementary school, sequential experiences of first- and second-generation segregation likely triggered a cycle of cumulative disadvantage for respondents' middle school educational outcomes. This article contributes to the literatures on the structural antecedents of school success and failure, the ways that many positive desegregation effects are undermined by tracking, and how first- and second-generation segregation contributes to maintaining the race gap in school outcomes.