This study investigated relations between preschoolers' pretend play, examiner-rated adjustment, and teachers' reports of educational and social adjustment in a large and racially diverse sample. Preschoolers (N = 171; [mean age]= 49.25 months, SD = 2.76; 89.5% non-White; 50.9% female) completed a standardized assessment of pretend play during a laboratory visit and teachers rated their academic and relational adjustment 3 months later. Interactive effects by child race were evaluated in light of prior suggestions that relations between children's creative expression and teacher-rated adjustment may vary by child race. There were no significant race differences in observers' ratings of preschoolers' pretend play, examiners' ratings of child adjustment, or teachers' ratings of child adjustment. Imaginative and expressive play features were positively related to examiners' ratings of child ego-resilience for all children in the laboratory setting. However, child race moderated relations between these same play features and teachers' ratings of preschooler adjustment in the classroom, even after child age, child IQ, family socioeconomic status, teacher-child racial congruence, teacher familiarity with the child, and child gender were held constant. Among Black preschoolers, imaginative and expressive pretend play features were associated with teachers' ratings of less school preparedness, less peer acceptance, and more teacher-child conflict, whereas comparable levels of imagination and affect in pretend play were related to positive ratings on these same measures for non-Black children. These results suggest that teachers may ascribe differential meaning to child behaviors as a function of child race. Implications for child development, teacher training, and early education are discussed. (author abstract)