Youth with conduct problems present frequently depressive symptoms. Academic skills are thought to be a mediating variable by which conduct problems could lead to depressive symptoms. No studies have longitudinally compared this model among school-aged boys and girls with different levels of conduct problems. Cascade models were tested to examine the relations between conduct problems, depressive symptoms, and academic skills over a 3-year period, and whether the severity of conduct problems and gender moderated these associations. Participants were 381 children presenting early clinically significant conduct problems (44.9% female) and 363 children with low levels of conduct problems (48.8% female). While results did not show any cascade or indirect associations, they revealed different direct links between conduct problems or depressive symptoms and academic skills in the four groups. These findings suggest that conduct problems severity and gender differences should be considered in treatment planning.