This research aims to: (1) reveal the background of life and analyze the role of K.H Ahmad Dahlan in the trajectory of Indonesian history; (2) review entrepreneurship values of K.H. Ahmad Dahlan; (3) analyze how entrepreneurial values of K.H. Ahmad Dahlan can be actualized in historical learning in the school. This research is qualitative study with historical approach. The subject and object of this study are related to the dimension of history, so it is necessary to reconstruct with a historical method. This study employed a document study consisting of primary and secondary sources. In addition, it also used interviews as reinforcement. Interviews were conducted with several Muhammadiyah figures and expert figures in K.H. Ahmad Dahlan's life. The results showed that, first: K.H Ahmad Dahlan was born and grew up in an environment that has a high level of religiosity. The religious family environment has formed his personality to be a person with good manners and characters and had a high learning spirit. Even though he did not have a formal school education, he learned from his father, family and other scholars. Second, his entrepreneurship values that can be emulated consist of action-oriented, creative, leadership, independent, risktaking and hard-working values. All these values were manifested in his life. Third, the actualization of K.H. Ahmad Dahlan's entrepreneurship values in order to contribute to the world of education is realized to inspire history teachers that their task does not only present a series of facts and events, but also build understanding and awareness for students about the meaning behind events, including what values are contained in these historical events.