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The early history of the legal battle by African Americans for access to Oklahoma’s territorial schools has not been told. Beginning in Oklahoma’s territorial days (1889-1906), African American families fought against the narrowing of educational opportunities; one of the key locations of that fight was the territorial courtroom. Through an examination of the historical context and an analysis of legal cases as primary sources, the paper examines the ways African Americans resisted. Through a pragmatic legal approach, they first challenged the denial of their access to integrated education and then they demanded equitable funding for all-black schools. This paper seeks to bring to light the story of these legal battles and the story of a contested territory.