School bullying has always been a global concern. Little is known about the joint occurrence of bullying perpetration and victimization. Using a large sample of Hong Kong secondary school adolescents (N = 1,880), this study investigates the overlap between these two experiences. Grounded by the theoretical propositions of Hirschi’s social control theory, the adolescents’ familial and school bonding, along with their psychological characteristics (i.e., self-efficacy, empathy, and prosocial behavior), are examined. Findings reveal that different bullying perpetration and victimization subtypes are positively correlated, and multivariate analyses confirmed the link between these two experiences. Bivariate probit models indicate a considerable degree of overlap between bullying perpetration and victimization. Being a female with poor empathic understanding, low level of prosocial behavioral manifestation, weak family attachment and perception of a harmonious school, poor sense of school belonging, and overall negative school experience and involvement are found to be significant risk factors for the joint occurrence of bullying perpetration and victimization. Practical implications, study limitations and future research directions are also discussed.