The purpose of the study was to examine the association between affective empathy, cognitive empathy, and gender on cyberbullying among adolescents. Participants were 396 adolescents from Singapore with age ranging from 12 to 18 years. Adolescents responded to a survey with scales measuring both affective and cognitive empathy, and cyberbullying behavior. A three-step hierarchical multiple regression analysis was used with cyberbullying scores as the dependent variable. Gender was dummy coded and both affective and cognitive empathy were centered using the sample mean prior to creating interaction terms and entering them into the regression equations. The testing, probing and interpretation of interaction effects followed established statistical procedures. Results from hierarchical multiple regression analysis indicated a significant three-way interaction. At low affective empathy, both boys and girls who also had low cognitive empathy had higher scores on cyberbullying than those who had high cognitive empathy. This pattern of results was similarly found for boys at high affective empathy. However, for girls, high or low levels of cognitive empathy resulted in similar levels of cyberbullying. Implications of these findings include the need for empathy training and the importance of positive caregiver-child relationships in reducing cyberbullying behavior among adolescents.