Children with disabilities play less often and demonstrate fewer varied pretend play behaviors than children with typical development. A multiple-probe design was used to examine the relation between teachers’ use of the system of least prompts and contingent imitation and the acquisition, maintenance, and generalization of pretend play and related behaviors by four children with disabilities. Results indicated the teachers’ use of the intervention package was functionally related to increases in the children’s frequency and diversity of pretend play and related behaviors. Children also maintained responses in sessions without prompts and generalized across toys and contexts. The findings replicate previous studies on adult prompting of pretend play and extend the literature by assessing generalization of children’s pretend play across contexts and measuring intervention and implementation fidelity. Overall, this study provides a strong argument for engaging in systematic instruction of play, including pretend play, for children who do not display such behaviors.