Research framed by Bronfenbrenner's ecological systems theory, suggests that neighborhood and school contextual factors greatly influence adolescent outcomes. While this research examines the multiple contexts that impact adolescent development, missing from the literature is an assessment that uses multiple data sources. Therefore, the present study used adolescent survey, school records, and Census data to examine the effects of perceived and structural neighborhood and school factors longitudinally. Additionally, many neighborhood-level studies treat demographic variables as covariates. But since poverty can be structurally portrayed in various ways, neighborhood-level population density was included as a predictor variable. The present study examined the effects of neighborhood and school context on adolescent achievement, attendance, and school violations. It was hypothesized that population density, perceived neighborhood connectedness, safety, and school belonging would predict poorer student academic outcomes. A linear mixed model was used for the analyses. The study's sample came from the Mobile Youth Survey (MYS), a fourteen-year longitudinal research project conducted in the low-income and public housing neighborhoods of Mobile, Alabama. The sample was over 99% African American and participants were between the ages of 10 to 18. To assess participants longitudinally four waves of MYS data (2006-2009) were paired with subsequent academic years. Results indicated that school context explained a greater amount of the variance in the outcome variables in comparison to neighborhood context. Results also indicated that adolescent perceptions of neighborhood connectivity predicted higher reading achievement and increased school violations. Further, higher perceptions of school belongingness predicted increased reading and math achievement and lower rates of school violations and absences. High neighborhood-level population densities predicted increased student absences. Additionally, non-African American students had higher rates of absences. Lastly, students who qualified for free lunch had more school violations. Consistent with Bronfenbrenner's ecological systems theory, the present study highlights the importance of examining multiple contexts when assessing adolescent outcomes. The results reiterate the complex nature of adolescent development. In future MYS and neighborhood-based studies, it may be favorable to compare different school-based policies and examine the influence of adolescent peer pressure.