This exploratory study examines the relationships between self-esteem and psychological adjustment among 19 adolescents with Asperger syndrome and 19 typically developing adolescents using a model developed by Harter. The groups were matched for age (mean 13 years), sex (M:F 16:3) and ethnicity (white British). Participants completed four quantitative measures examining self-competencies, social approval, anxiety, depression and self-worth. Findings revealed significant group differences: the adolescents with Asperger syndrome perceived themselves to be less competent in social and athletic domains, and to receive less peer approval. Logistic regression analyses indicated that the variables studied were particularly relevant in distinguishing group differences and worked together in predicting group membership. Indeed the variables in the final model accurately predicted group membership for all individuals in the sample. Exploratory hierarchical multiple regression analyses suggested that the two groups had different patterns of relationships between measures of self-competencies, social approval and psychological outcomes.