Based on the study of seventy-four middle school children of mostly Filipino and part Hawaiian heritages, this article explores the relationships of children's thinking styles, play preferences, and school performance. Using the Group Embedded Figures Test, the Articulation of the Body Scale, and written responses to three questions, the authors found significant relationships between children's field-independent or field-dependent thinking styles and play preferences; play preferences and academic performance; thinking styles and academic performance; and thinking styles and cultural setting. They also discovered that children's preferences for sports related, both positively and negatively, to their scores on state-mandated tests for language and math; that children who preferred unstructured play activities tended to achieve academic success; and that cultural values were correlated to thinking style. The authors argue that their study has applied value for educators because it relates children's play preferences to other aspects of their life experiences, which can help school policy makers decide the extracurricular activities and the types of play they should encourage. (Contains 9 figures.)