Sleep problems are associated with problematic adjustment in toddlers, but less is known regarding the direction of association between specific sleep problems and adjustment. To address this gap, we used data from the National Institute of Child Health and Human Development Study of Early Child Care and Youth Development (N = 1001) to examine reciprocal associations between sleep problems and behavior problems from 24- to 36-months. Results from cross-lagged path models suggested specificity of associations between type of sleep problem and behavior problem. Specifically, there were reciprocal associations between trouble getting to sleep and internalizing problems, and unidirectional links between externalizing problems and bedtime resistance from 24- to 36-months. Internalizing and externalizing problems at 24 months, however, predicted increases in bedtime resistance from 24- to 36-months for boys, but not girls. Findings highlight specific relations between sleep problems and internalizing and externalizing problems during toddlerhood, and the importance of examining sex differences.