Cyberbullying may sometimes be an extension of traditional bullying. However, some particular features of cyberbullying suggest that it may have a distinct causal pathway, due to the social context of a virtual environment within which peer social processes occur. Moreover, boys and girls may perceive and respond differentially to their social context, which may heighten the risk for victimisation. This study aimed to describe how the perceived relational context (school, peers and family) may influence the probability of becoming a victim, in both offline and virtual contexts, among boys and girls. A questionnaire, measuring school climate; global, family and peer self-esteem; loneliness in relationship with parents and peers; and victimisation in traditional direct, traditional indirect and cyberbullying, was completed by 2326 Italian adolescents (mean age 13.9 years). For traditional victimisation, significant predictors were loneliness in relations with peers and a negative perception of school climate, in both males and females, while younger age (for direct victimisation) and lower global self-esteem (for indirect victimisation) were predictors for males only. For cybervictimisation, involvement as either a direct or an indirect victim was a very strong predictor for both males and females, but with an element of distinction compared to traditional victimisation, as lower self-esteem in family relationships was a predictor of cybervictimisation for males, while parent loneliness was a predictor for females. Implications for understanding the continuity/discontinuity between traditional bullying and cyberbullying, and for the development of intervention strategies, taking into account some differences by gender, are discussed.