Playing and moving are central in young children's lives. Allowing the children to experience the natural and man-made elements in their school environment would develop their cognitive, physical and social abilities. This study investigates the impact of playing in outdoor play space on physical skills or motor development of kindergarten children. The outdoor play spaces of four kindergartens's playground were selected to be evaluated in the case study afterwards. The research aim is to identify the landscape features (natural and man-made) in the playground areas that offer challenge in children play. Data of the children performances were elicited using a phenomenological approaches by employed three major strategies include interviews, observation and behaviour mapping as well as children participatory drawing project. The data gathered from two source : teachers and staffs as well as the kindergarten's children. The data were analysed using descriptive statistics and content analysis. The data advocated that the children performed dynamically during play activities in outdoor play area particularly when they attached to the natural environment. Based on Theory of Affordances applied in this study, the result showed that the effects of outdoor play space on children's play and performances were higher when they experienced the natural and man-made elements directly. The study concluded that the landscape features (natural and man-made) in outdoor environments fostered the physical skill of kindergarten's children and it should be incorporated in the design of a kindergarten.