Traditional school bullying and cyberbullying are growing concerns worldwide. Research has been devoted to understanding the etiology of bullying behaviors. Using a large sample of secondary school adolescents in Hong Kong (N = 1,893), this study explores gender differences in mean levels of traditional school bullying (i.e., physical and verbal forms of bullying, and extortion and exclusion) and cyberbullying (i.e., overt and relational aggression) behaviors, and psychosocial characteristics (i.e., self-efficacy, empathy, prosocial behavior, family bonding, perception of a harmonious school, sense of belonging in school, and positive school experiences and involvement). The differential role of psychosocial characteristics in types of bullying perpetration is also examined. Findings indicate that the perpetration of traditional school bullying and cyberbullying behaviors are positively correlated, and male adolescents reported higher levels of bullying perpetration than female adolescents. Multivariate findings reveal that, to some extent, male and female adolescents shared a similar set of psychosocial risk factors of bullying perpetration, especially in the perpetration of traditional school bullying. The findings of this study may have important implications for practice in regard to minimizing, if not entirely preventing, through the joint efforts of the family, school, and social service systems, the propensity of adolescents to engage in the perpetration of bullying behaviors.