Objective: This study aims to classify the types of problem behavior among high-risk adolescents and explore how the parent-child relationship influences the types of adolescents’ problem behavior depending on the gender of students. Methods: The samples included 322 high-risk adolescents (169 male and 153 female students) attending middle and high school. The SDQ-Kr, Ego Resilience, and Parent-Adolescents Relationship were measured. Results: First, the types of high-risk adolescents’ problem behavior were classified into three groups: “Hyperactivity/inattention-Emotional control problems”, “Peer conformity-Conduct problems”, and “Anxiety/depression-Delinquency coexistence”. Second, more high-risk male adolescents belonged to the “Peer conformity-Conduct Problems” and “Anxiety/depression-Delinquency coexistence” groups than female adolescents. More female adolescents belonged to the “Hyperactivity/inattention-Emotion regulation” group than male adolescents. Third, for both high-risk male and female students, the less their parents failed to provide consistent and appropriate discipline, the more likely they were to belong to the “Anxiety/depression-Delinquency coexistence” group. Conclusions: To provide effective intervention for high-risk adolescents, customized intervention programs differentiated according to gender and customized parent education programs differentiated according to their children's problem behavior types should be developed.