The category of ‘history painting’ did not exist in Japan until the Meiji era. Following the introduction of the concept of fine arts into Japan from the West, Japanese adopted the category of history painting and began depicting their own history. In this paper, I will introduce a series of history paintings produced by painters who were working with Okakura at the Tokyo School of Fine Arts. These paintings were purchased in the 1890s by the First Higher School, the top educational institution in the country prior to the establishment of the University of Tokyo, and are now in the collection of the Komaba Museum. 1889 was remarkable year for history painting in Japan. The Meiji Constitution came into effect, followed shortly afterwards by issue of the Rescript on Education. This paper will examine the social and political context of the last decade of the nineteenth century when the history paintings were commissioned by the First Higher School, paying particular attention to the educational philosophy of the school. By comparing the history paintings with illustrations published in contemporary history textbooks, I conclude with a consideration of the meaning of ‘history painting’ in Meiji period Japan.