The study explored the relationship between situational leadership and diversity management skills of school heads in public secondary schools of Davao Oriental Division. Also, it investigated the association of the involved variables and the domains of situational leadership of school heads that significantly influence their diversity management skills. With the use of probability sampling, 137 public secondary teachers were selected as the respondents. Utilizing the descriptive-correlational survey method, the data collated were analyzed through the use of Mean, Product-Moment correlation and Regression Analysis. Results revealed that there was a very extensive situational leadership and extensive diversity management skills of school heads as perceived by the respondents. Furthermore, there was a significant relationship between situational leadership and diversity management skills of school heads. Specifically, delegating has the greater impact on the diversity management skills of school heads. Moreover, all domains of situational leadership, namely, directing, coaching, supporting, and delegating were found to have significantly influence the diversity management skills. Based on the findings, it was further suggested that higher officials in the Department of Education may identify means on how to strengthen the situational leadership of school heads which would boost their diversity management skills. More so, future researchers may further explore the involved variables considering other factors and research methods.