This paper explores the particular aspects of learning which might be supported through playful activity and reviews research and theory which link children’s play, and particularly pretence or symbolic play, to the development of metacognitive and self-regulatory skills. Three studies are reported, one observational and two experimental, which have explored this relationship. The observational study involved the video-recording of 582 metacognitive or self-regulatory ‘events’ within Foundation Stage settings. The two experimental studies replicated in different learning domains the classic study of Sylva, Bruner and Genova (1976), which contrasted the problem-solving performance of 3- to 5-year-old children who had experienced a ‘taught’ and ‘play’ condition. Evidence from the present studies reported and other studies supports the view that play, and particularly pretence or symbolic play, which might be with objects or other children, is particularly significant in its contribution to the development of children as metacognitively skilful, self-regulated learners. Evidence from the observational study indicated that child-initiated playful activities, in small groups without adult supervision, supported the greatest proportion of self-regulatory behaviours. The experimental studies suggested that the experience of the ‘play’ condition was particularly effective in preparing the children for effortful, problem-solving or creative tasks which require a high level of metacognitive and self-regulatory skill. Metacognitive and self-regulatory development is crucially important in the development of academic skills which involve intentional learning, problem-solving and creativity. An understanding of the relationship between pretend or symbolic play and self-regulation is also helpful in providing clear guidelines for adults working with young children as regards their role in supporting and encouraging play in educational contexts.