In this paper we combine a philosophical theoretical analysis with human movement science empirical studies, in order to provide a better understanding of the possible links between free play and creativity. We deal in particular with some dialectical dynamics inherent to free play: the relation between rules and freedom, spontaneity which often leads to imitation, the presence of a purpose as a necessary element to makes novelty creative, innovation as an essential part of adaptive processes. We remark the topic into a developmental perspective including the role of play tutoring. We advocate an interdisciplinary criticism for approaching the paradigm of free play and creativity. Our aim is to show that free play in itself does not always and necessarily imply creativity, but can easily foster it in the presence of certain specific conditions.