The first purpose of the current study was to examine the relationship between children's active play imagery and two developmental outcomes, personal/social skills and cognitive skills. The second purpose was to examine the relationship between children's active play imagery and self-confidence in active play. A total of 105 male and female children (Mage = 9.84, SD = 1.41) were recruited from various summer programs, and completed inventories that assessed their active play imagery (i.e., capability, social, and fun), positive personal development (i.e., personal/social skills and cognitive skills), and self-confidence. Examination of the scales' psychometric properties indicated poor reliability for the cognitive skills subscale; therefore it was excluded from further analysis. Multiple regression analysis revealed that all three active play imagery types (capability, social, fun) were positively and significantly related to personal/social skills, accounting for 26% of the variance. Specifically, capability imagery and social imagery emerged as the strongest individual predictors of personal/social skills. Further, regression analysis showed that both capability imagery and fun imagery were positively and significantly associated with self-confidence, accounting for 18% of the variance. In particular, fun imagery was found to be the strongest individual predictor of self-confidence. This study highlights the usefulness of imagery in fostering important developmental outcomes and self-confidence among children. To this end, child practitioners should consider implementing imagery workshops in school, clinical, and community settings.