The present study investigated to what extent the members of adolescents’ peer groups share similar educational expectations, and to what extent overall and school-related adjustment are associated with these expectations. Three hundred and ninety-four ninth-graders facing the transition to secondary education filled in questionnaires measuring their short-term and long-term educational expectations, and their academic achievement, learning difficulties, negative attitudes towards school, problem behavior, and self-esteem. Multilevel modeling showed that peer group members shared similar educational expectations. Among girls, adjustment typical of the peer group was associated with the group members’ educational expectations. By contrast, among boys, only problem behavior typical of the peer group was associated with the group members’ educational expectations.