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School belonging is critical for adolescents’ academic and social development, which is significantly shaped by peer relationships. However, less has been understood regarding unique roles of multiple dimensions of peer relationships (i.e., quantity vs. quality, relations with group vs. with individual best friend), and the extent to which the roles may vary by individuals’ social characteristics, particularly shyness, which has been found influencing various aspects of school adaptiveness. The current study included 156 high-school students (Girl = 37.82%; Mage = 15.84, SDage = 4.92), where 43 shy students were identified based on a peer nomination task. Findings demonstrate the importance of peer relationship quality, particularly group-based, on adolescents’ school belonging, and evidence the differences between shy students and others.