In this research maternal psychological and behavioral control and its relationships with adolescents' friendships, psychosocial and academic adjustment and the mediator role of self esteem were investigated in a proposed model. Participants were 409 adolescents (200 girls, 209 boys; Mage = 14.61, range = 12 to 18 years) from 7th to 10th grade of primary and high schools. All adolescents were coming from middle class families. Measurements were Aggressive and Prosocial Behavior Questionnaire, Self Perception Profile for Adolescents, Behavioral Control Questionnaire, Psychological Control Questionnaire, Deviant Friends Questionnaire, Prosocial Friends Questionnaire, Loneliness and Social Dissatisfaction Scale, UCLA Loneliness Scale, and perceived school success (evaluated by 5 point scale). Since preliminary analyses revealed different type of patterns for both boys and girls, structural equation models were conducted separately. Results showed that behavioral control was related. with increased self-esteem, however, psychological control was not both for boys and girls. In addition, psychological and behavioral control related with other outcome behaviors in different ways according to gender. Increased psychological control related with increased internalization and externalization behavior problems and having more friends that are deviant in girls; externalization behavior problems and more friends that are deviant in boys. Perceived behavioral control was positively correlated with perceived school success in girls, and having prosocial friends in boys. Increased behavioral control was related with decreased internalization/externalization behavior problems and less deviant friends in boys. Findings were discussed in terms of type of maternal control and culture.