During imaginative play, children may learn foundational skills important for academic success. Indeed, imaginative children, high in fantasy orientation (FO), may have advantages in skills that support positive classroom and social behavior. Yet findings are mixed regarding the classroom behavior of children high in fantasy orientation. The purpose of the current study was to examine the cognitive and social skills of children who typically engage in imaginative play in comparison to their peers in classroom contexts across multiple informants: child, teacher, and classroom observers. Ninety preschoolers and their teachers completed measures of fantasy orientation (FO), self-regulation, emotion knowledge, vocabulary, and social competence. Further, observers reported on children’s classroom behaviors. Research Findings: Cluster analyses revealed children with higher scores on direct assessments of executive functioning, emotion knowledge, and vocabulary had higher FO. Additionally, children whose teachers reported them as socially competent had higher FO. Finally, children who were rated by classroom observers as high in emotive social play, peer conversation, and physical activity had higher FO. Thus, across multiple informants, children high in FO and imaginative play exhibited higher cognitive and social skills in the classroom. Practice or Policy: These findings suggest that children high in FO may have benefits in skills that are related to positive academic skills in comparison to peers. Curricula should continue to examine the utility of imaginative play as a context to support cognitive and socioemotional development. (author abstract)