This study examined household income and maternal cognitive stimulation as moderators of the association between family structure and 48-month-old child emerging literacy and math skills. The data set was the Early Childhood Longitudinal Study–Birth cohort (N = 7,300). Controlling for selection factors (race/ethnicity, child gender, maternal education, maternal depression, child attendance in preschool/day care, and 9-month child cognition), the study found support for the moderation hypothesis for household income and maternal cognitive stimulation. The main take-home message was that resources such as household income and mothers’ cognitive stimulation seem to be more strongly and positively associated with early literacy and math skills among children with married parents in comparison to children living in stable single-mother households, stable cohabiting households, or households in which mothers transition from married to single parent. Cognitive stimulation partially mediated the moderating effect of income on stable single-mother household. Implications for research and programs are discussed.