Despite the importance of play as an instructional medium and its contribution on children's learning, development and creativity at all levels of education, research data extracted from Greek literature demonstrate that teaching does not depend on play at the extend that it should. The current study was conducted during the 2019 academic year and investigates on the views of current Kindergarten Educators (N:100) working on faculties of the Region of Epirus as well as Senior Students (N:100) at the Department of Early Education of the University of Ioannina, and it scrutinizes on the planning and evaluation of the educational process in terms of play within preschool cognitive environments and also on the role play holds in the Kindergarten’s educational procedure. The findings of this research pointed out the significance of play’s role towards learning and development of preschool aged children. Nonetheless, the current Educators do not acknowledge the importance of children’s participation in the actual planning of play scholar environments in opposition to the prospective Educators who deem such as vital. Both groups, Educators and Students show an encouraging attitude towards their pupils when it comes to them desiring to design play activities, however the Students show limited confidence on educational planning issues, due to their lacking teaching experience within actual Kindergarten faculties. Educators as well as Students who have undertaken training courses regarding the educational merit of play, evaluate children’s learning through play to a higher degree than their colleagues who have not attended such courses. Finally, the current research points out the pedagogical expertise of the Instructors needed towards a more comprehensive use of play in the educational praxis.