Several heuristic models posited that environmental stress disrupt adolescents' engagement and performance in school, but few studies have identified police as a source of such stress. We examined whether police stops, direct and vicarious instances, predicted decrements in adolescents' grades via their psychological (i.e., depressive and anxiety symptoms) and health (i.e., sleep problems and self-rated health statuses) stress responses. We also examined whether the observed correlates varied across ethnic-racial and gender groups. To do so, we used two waves of longitudinal survey data from the Fragile Families and Child Well-Being Study. Children completed surveys when they were, on average, ages 9 and 15. Results illustrated that direct and vicarious police stops at age 15 predicted lower grades contemporaneously, controlling for adolescents' self-rated health, sleep, and performance on the Woodcock-Johnson tests at age 9. Psychological distress, sleep problems, and self-rated health at age 15 partially mediated the relations between police stops and grades. The negative consequences of vicarious police stops were specific to the boys and girls of color; vicarious police contact did not predict adolescents' grades for White boys and White girls. We discussed the implications of our results as they pertain to policing and adolescent development.