Eating disorders, and related issues (e.g., body dissatisfaction, weight control behaviors), represent pressing and prevalent health problems that affect American adolescents with alarming frequency and potentially chronic consequences. However, more longitudinal research is needed to elucidate the developmental processes that increase or maintain risk for, and that protect against, eating- and weight-related problems among adolescents. Accordingly, the current study used longitudinal data from 1,050 male and female (68.0 %) adolescents (Grades 9–11)—the majority of whom were European Americans (72.2 %)—who participated in the 4-H Study of Positive Youth Development to (a) describe trajectories of adolescents’ eating pathology and body dissatisfaction, (b) identify individual and contextual correlates of these pathways, (c) examine whether trajectories of eating pathology and body dissatisfaction related to adolescents’ depressive symptoms, and (d) elucidate whether sports participation moderated associations between specific trajectories of eating pathology and body dissatisfaction and adolescents’ depressive symptoms. Results suggest that the diverse pathways of eating pathology and body dissatisfaction that exist across middle adolescence, in combination with adolescents’ sports participation, have important implications for the positive and problematic development of our youth. In addition, the findings underscore the need to evaluate the interindividual differences that exist in regard to how sports participation may relate positively and negatively to developmental outcomes.