This study aimed at examining the existing relation among parenting, cultural value orientation, and bullying propensity at school. The participants (N = 231) were early adolescents randomly selected from 11 different schools in urban and rural areas of Cyprus. The results showed that a statistically significant relation exists between parental authoritarianism and child bullying propensity. In contrast, no such relation was found between bullying and the authoritative parenting style. An argument that has been proposed by prior research is that bullying incidents in collectivistic types of cultures can be attributed to the authoritarian parenting style that is widely used and valued in such cultures. However, authoritarian parenting was found to be positively correlated with the vertical dimension of both collectivistic and individualistic value orientation. Further, the results of this study show that children with vertical cultural value orientation are more likely to engage in bullying only when they come from families that use authoritarian parental styles. These findings are discussed in terms of the significance of power distance in the prediction of bullying behavior.