Growing evidence highlights the importance of executive functions (EFs) for optimal development. Unfortunately, existing literature documents compounding deficits in EF due to the stressors associated with poverty. Recent research supports a positive relationship between pretense and EF, but few studies have examined the longitudinal association between these variables in a low-income sample. As such, the current study investigated whether pretend play behaviors among a sample of 191 Head Start preschoolers predicted EF outcomes in first grade, and whether pretend play mitigated the adverse consequences of cumulative risk on children’s EF development. Results revealed a positive, prospective relationship between pretense in preschool and EF in first grade. In addition, pretend play moderated a negative association between cumulative risk in preschool and EF outcomes in first grade, with the association being weaker for children who engaged in more pretend play relative to those who engaged in less pretend play. Follow-up analyses suggest that pretend play may be particularly important for the inhibitory control aspect of EF in this sample.