The present study was conducted to predict bullying roles over a 6-year time period and across contexts differing in the degree of peer hierarchies. Out of two representative data sets from primary (N = 1525) and secondary school (N = 2958), 282 children (156 boys; 126 girls) were followed up longitudinally. Self-reports on bullying experiences and peer reports about social status were assessed by a structured individual interview (in primary school) and by questionnaire given classwise (in secondary school). Risk analyses showed that only a bully role in primary school yields a risk of being sustained in secondary school. However, victims in primary school classes with a more pronounced degree of hierarchical structuring proved stable in their role while the victim role was unstable from primary school classes with low hierarchical structuring. This interaction did not apply to bully role stability. Differential characteristics of the victim and the bully role in primary school and secondary school settings are discussed.