Parental monitoring, child social competence, and child academic success were examined as mediators explaining the relationship between Oregon's Model of Parent Management Training (PMTO) and long-term changes in deviant peer association for an at-risk sample of divorced mothers of 6-10 year old boys. Participants included a community sample of 238 boys and mothers. Mother's mean age was 34.7 years at the start of data collection, and boys mean age was 7.8 years. Multi-method, multi-informant methods were used to examine skilled parenting and parental monitoring, as well as child factors, including social competence, academic success, and deviant peer association. Intervention was found to positively impact average levels in deviant peer association across time. Parental monitoring did not mediate the relationship between intervention and changes in deviant peer association. Parenting skill induced changes in social competence and academic success were not found to mediate the relationship between PMTO and future deviant peer association. However, children who were ranked higher on social competence and had stronger academic skills demonstrated lower levels of deviant peer association and reduced risk for persistent affiliation with antisocial peers. These results support the need to ascertain other mediating factors contributing to the increasing, long-term benefits of PMTO. Further implications for prevention and intervention are discussed.