This study aims to investigate the relationship between dramatic play and self-regulation in preschool age. The descriptive correlational methodology is utilized using three tools: dramatic play questionnaire, self-regulation scale (Head, Toes, Knees, and Shoulders), and children’s interviews. The sample of the study consists of 60 children aged 4-6 years. Quantitative analysis is done using the Pearson Correlation Coefficient, factor analysis, and multiple regression analysis. The interviews with children are qualitatively analyzed calculating frequency, and percentage of coded data. The findings reveal a significant positive correlation between dramatic play and self-regulation. Besides, it is found that self-regulation could be predicted through the dimension of interactions with others during dramatic play. The study also proves a defect in the quality of dramatic play in terms of social interaction, symbolism, and themes and roles practiced by children. In the light of these results, the researchers suggest that mothers and teachers’ awareness of the importance of quality dramatic play should be enhanced, to enable them to allow and plan for quality play. Also, allowing flexibility in preschool programs could support teachers’ efforts in enhancing play engagement and development. Finally, this study has facilitated further research in the Arabian region, since it highlighted a valid, cross-cultural tool for measuring self-regulation in the Arabic language.