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This article investigates whether gender differences in children’s math, reading, and behavior problems vary across mothers’ education and family structure. Using data from the National Longitudinal Study of Youth-Children and Young Adults (N > 6,200; age range = 5–14; 51 percent female; 30 percent Black, 20 percent Hispanic, and 50 percent other ethnic backgrounds), we hypothesized that boys growing up with less educated mothers and in single-parent families may lag behind girls more significantly in reading and behavior problems. They may be less ahead in math than their peers from more advantaged backgrounds. Our findings demonstrate this heterogeneity of gender differences by maternal education but not by family structure. This may indicate that cultural norms associated with gender play a significant role in explaining the observed heterogeneity across family circumstances. We replicated these findings for academic achievement using data from the Early Childhood Longitudinal Study Kindergarten Class 1998–1999.