This purpose of this study was to explore the moderating influence of gender on the relationship between child maltreatment and internalizing symptoms (e.g., affective and somatic problems) and externalizing behavior (e.g., rule breaking behavior and aggression) among children aged 7-12 years old. Using a longitudinal comparison group design and a sample of 300 youth of which 56% (n = 168) had substantiated cases of child maltreatment, results of a structural equation modeling revealed that internalizing symptoms exerted a mediating influence that was conditioned by gender. Only girls' internalizing symptoms were found to mediate the link between child maltreatment and externalizing behavior while a direct relationship between maltreatment and externalizing behavior was found among boys. These findings provide evidence for gender differences in the pathways between being child maltreatment and maladaptive thoughts, feelings, and behaviors. Thus, adapting evidence-based strategies that target gender specific internalizing behaviors and externalizing behaviors among maltreated youth may significantly reduce the risk of short and long-term maladaptive behavior.