This study examined the longitudinal relationships between children's playfulness, creative thinking processes, and academic skills. Participants were 150 Chinese kindergarten children (52.7% boys; Time 1 age range = 4-5 years) and their parents. At Time 1, the parents reported demographic information and rated children's playfulness (social and cognitive spontaneity) by completing the questionnaire. Children were administered behavioral measurements of creative thinking processes (convergent and divergent thinking), Chinese word reading, and mathematics skills (forward counting, backward counting, number word comparison, arithmetic addition, and arithmetic subtraction). One year later, at Time 2, children completed the same behavioral assessments again. Results from a path analytic model revealed that the indirect relationship between playfulness at Time 1 and mathematics at Time 2, mediated through convergent thinking at Time 1, was positive and significant. Moreover, children's convergent thinking and mathematics skills reciprocally predicted each other. These findings suggest that playful kindergarten children might display better creative thinking and academic skills over time. Furthermore, the results highlight how encouraging children's playfulness and implementing play-based mathematics activities may nurture their creativity and academic skills.