Similar to countries in Europe and the Americas, risky play is a feature in Japanese early childhood education and care. This study investigated the perceptions and practices of Japanese early childhood education specialists with respect to risky play in order to ascertain whether their childhood experiences influenced their attitudes toward preschoolers' risky play. Data were collected from a survey, and findings showed that childhood experiences influenced respondents' practices regarding restricting risky or unsafe play. Among the various types of risky play, play at great heights received the most references regarding both childhood play and current activity restrictions. The research concluded that 1) regular and ongoing discussions among practitioners are crucial given their diverse experiences and the disparity of perceived risks between players and supervisors; 2) policy is required to provide children with rich experiences of risky play because of insufficient opportunities in their early childhood environments. Overall, the research highlights the importance of cultural and environmental backgrounds in practitioners' perception of risky play.