We examined childhood social withdrawal and aggression as predictive of adolescent maladaption, comparing and contrasting social and emotional outcomes associated with aggression and social withdrawal. We also focused on childhood social competence as a predictor of adolescent adaptation. The sample comprised 60 children for whom a complete data set was available at both ages 7 and 14 years. The predictors were aggregated measures of social withdrawal, aggression, and social competence derived from three sources—behavioral observations, peer assessments, and teacher ratings. The outcomes focused primarily on markers of internalizing and externalizing problems. The results indicated that childhood social withdrawal uniquely and significantly contributed to the prediction of adolescent loneliness, felt insecurity, and negative self-regard. Aggression predicted adolescent delinquent activity; social competence predicted felt security in the peer group and substance use in adolescence.