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Objective Adolescent cyberbullying and high-risk behaviour outcomes has been a major concern in the last few years. Gender discrepancy is an important component that predicts the outcomes. This study aimed to elaborate and identify the association between cyberbullying experience and high-risk behaviour outcomes based on gender differences among adolescents in Indonesia. Method: A cross sectional study that involved junior and senior high schools in Jakarta. There were 2917 adolescents who took part in this study. The cyberbullying questionnaire was used to identify the cyberbullying experienced. High-risk behaviour included in this study was tobacco smoking, alcohol consumption, and self-harm behaviour. Chi-Square test and odds ratio analysis were applied through SPSS for Mac. Results: The highest proportion in this study was composed of adolescents of both genders who acted as victim/perpetrator (52.25%). Adolescent males who indulged in cyberbullying showed an increased risk for cigarette smoking (OR = 2.97); male adolescents who were victims and victim/perpetrator of cyberbullying had a higher risk to consume alcohol (OR = 2.96 & OR = 6.93). Meanwhile, the risk of self-hurting behaviour increased for both female and male with cyberbullying victimization (OR = 3.68 & OR = 2.97). Female adolescents who acted as victim/perpetrator had a higher risk of suicidal thoughts and attempting suicide (OR = 1.90 & OR = 2.11); and they were also at risk of consuming alcohol (OR = 2.84). Conclusion: Cyberbullying returned negative impacts on both genders of adolescents. Boys showed a greater tendency to externalize while girls showed a greater tendency to internalize. Mental health promotion that is designed specifically for both genders might address the adolescents’ needs.