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School readiness incorporates children's academic abilities and their ability to self-regulate in the classroom. Prior research shows that sleep is related to children's development of these skills, although the mechanisms through which sleep affects school readiness are not well understood. Research also indicates that economically disadvantaged children and children of color may have poorer academic and regulatory skills at school entry and may sleep less and sleep less well on a regular basis. The current study explores the role of sleep quantity and quality in young children's development of two skills critical for school success: self-regulation and academic abilities. This study intentionally focuses on a predominantly African-American, economically disadvantaged population, who may be at risk for greater sleep-related difficulties and lower school-related skills at kindergarten entry. It was hypothesized that a) young children with higher quantity and quality of sleep would show greater development of academic skills and self-regulation across one calendar year, b) the role of sleep in the development of these abilities would be relatively stronger among kindergarteners than among 1st graders, and c) the role of sleep quality and quantity in young children's development of academic abilities would be partially explained by the relation between sleep and self-regulation. Results provide mixed support for the hypotheses, indicating that sleep quality and quantity relate differentially to different school-related skills among kindergarteners and 1st graders. This study contributes research to help explain how and why sleep affects young children and may offer insights for caregivers and educators working to help children develop school-related skills.