This study disentangled the frequency and perceived severity of experienced bullying and victimization by investigating their associations with cognitive and affective empathy. Participants were 800 children (7–12 years old) from third- to fifth-grade classrooms who completed self-report measures of the frequency and perceived severity of their bullying and victimization and of cognitive and affective empathy. Results showed that the frequency and perceived severity of bullying were moderately correlated in the entire sample but unrelated within the subsample of bullies. Frequency and perceived severity of victimization were significantly and positively correlated in the entire sample (moderate effect) and the subsample of victims (small effect). Frequent, but not severe, bullies reported less cognitive empathy than non-bullies whereas both frequent and severe victims reported more affective empathy than non-victims. Within subsamples of bullies and victims, frequency of bullying was negatively associated with cognitive and affective empathy, and perceived severity of bullying was positively associated with affective empathy. Frequency of victimization was not associated with cognitive and affective empathy, but perceived severity of victimization was positively associated with both forms of empathy.