The current study further evaluated the association between rule-breaking behavior and academic performance by examining peer rejection and depressive symptoms as potential mediators of this association. Study hypotheses were examined using a sample of 147 school-age children (54.4% male) ranging from five to 13 years of age (M = 8.22, SD = 1.99). A meditational path model was estimated, and findings suggested that peer rejection mediated the association between rule-breaking behavior and academic performance two months later when also considering the stability of academic performance. That is, high levels of rule-breaking behavior were associated with high levels of peer rejection, which in turn was associated with poor academic performance. Depressive symptoms were not indicated as a mediator of this association. Findings and their implications are discussed.