To conduct a retrospective follow-up study of psychosocial adjustment and educational outcome in adolescents with a childhood diagnosis of attention deficit disorder (ADD) and a group of clinical controls. Groups included male and female subjects aged 14 to 18 years at time of follow-up with childhood diagnosis of ADD (cases; n = 48) versus other neurodevelopmental disorders (clinical controls; n = 37). Cases were also subdivided based on the presence of conduct disorder (CD) at follow-up. All groups were compared on measures of academic performance, self-esteem, behavior, alcohol and substance use, and adaptive functioning. Cases had significantly lower academic performance and poorer social, emotional, and adaptive functioning than clinical controls. Cases with CD had significantly lower academic performance, greater externalizing behaviors and emotional difficulties, and lower adaptive functioning than cases without CD. Cases with CD fared worse than clinical controls on self-report measures of behavior, socialization skills, and alcohol and substance use. These academic and psychosocial problems in adolescents with a childhood diagnosis of ADD suggest potential long-term ramifications for vocational and psychological functioning into adulthood. In addition, the presence of CD in some of these cases during adolescence appears to further increase the risk for maladaptive outcome.