Background Sleep has a significant influence on children's development. The objective of this study was to investigate Head Start children's sleeping patterns and the impact on cognitive and behavioural outcomes. Methods Using the 2009 cohort of the Head Start Family and Child Experiences Survey (N = 2,868), information on sleeping patterns was assessed through parent interviews. Cognitive outcomes were assessed using direct assessments (Peabody Picture Vocabulary Test‐IV, the Expressive One‐Word Picture Vocabulary Test, and Subtests of the Woodcock–Johnson III) in addition to teacher report. Behavioural outcomes were assessed through parent and teacher reports. A multiple regression analysis was performed for each outcome variable. Results Descriptive findings showed that 89% of children had a regular bedtime at least 4 days per week and that the average amount of sleep per night was 10.41 hr. White mothers were more likely than other racial groups to adhere to a consistent bedtime, and maternal employment predicted less hour of sleep per night. Multiple regression analyses revealed that disrupted sleep had a negative influence on cognitive outcomes, especially in areas of mathematical problem solving, receptive language, teacher‐reported literacy behaviours, and approaches to learning. Disrupted sleep was associated with the risk of misbehaviour by increasing teacher and parent ratings on aggressive behaviours, hyperactivity, and withdrawing in addition to decreased scores on overall social skills. Having an inconsistent bedtime negatively predicted expressive vocabulary and teacher‐reported literacy behaviours. Conclusions The findings of this study support the influential role of sleep on children's development. Sleeping through the night and having a consistent bedtime were found to be predictive of many areas of cognitive and behavioural development. Head Start staff can provide the supports to increase parental knowledge on appropriate child sleep practices.