Research has shown that learning disabilities are associated with internalizing problems in (pre)adolescents. In order to examine this relationship for math disability (MD), math achievement and internalizing problem scores were measured in a representative group of 1,436 (pre)adolescents. MD was defined by a discrepancy between math achievement and IQ. Internalizing problems were measured through a multi-informant (parents, teachers, self-report) approach. The results revealed that MD puts (pre)adolescents at a higher risk for internalizing problems. External and self-ratings differed between boys and girls, indicating that either they show distinct internalizing symptoms or they are being perceived differently by parents and teachers. Results emphasize the importance of both a multi-informant approach and the consideration of gender differences when measuring internalizing symptomatology of children with MD. For an optimal treatment of MD, depressive and anxious symptoms need to be considered.