This study examined associations between self-reports of sadness and anger regulation coping, reluctance to express emotion, and physical and relational aggression between two cohorts of predominantly African-American fifth (N = 191; 93 boys and 98 girls) and eighth (N = 167; 73 boys and 94 girls) graders. Multiple regression analyses indicated unique associations between relational aggression and expressive reluctance and sadness regulation coping. In contrast, physical aggression, but not relational aggression, was associated with anger regulation coping. These relations did not differ across gender, but the strength of the association between anger regulation coping and physical aggression varied by grade. Sadness regulation coping moderated the association between expressive reluctance and relational aggression. Conversely, anger regulation coping moderated the relation between expressive reluctance and physical aggression; however, the strength of this relation differed by gender. These findings have important implications for intervention efforts.