Some reports estimate that Old Settlers began migrating west by 1800, before the forced relocation of Cherokees by the United States in the late 1830s under the Indian Removal Act.

Following the western movement of the Cherokees, UKB traditional territories include the above-mentioned states with the addition of Arkansas, Illinois, Kansas, Missouri, Oklahoma, and Texas.

The UKB members are composed primarily of descendants of the "Old Settlers," Cherokees who settled in present-day Arkansas and Oklahoma around 1817.

[6] They were well established before most of the Cherokees were forcibly relocated by the United States government from the Southeast to Indian Territory in what became known as the 1838 Trail of Tears.

Under this legislation, they broke up communal tribal holdings and allotted plots of land to individual households, intended to be developed according to the European-American model of subsistence farming.

By assigning plots to individual households among the Five Civilized Tribes, they intended to encourage the European-American model of subsistence farming.

[8] Prior to World War II, the administration of President Franklin D. Roosevelt worked to strengthen Native American tribes by encouraging them to reconstitute their governments and adopt an electoral process.

Early elected leaders of the UKB were Levi Gritts, followed by John Hitcher, and the Reverend Jim Pickup, who served in the post-World War II era.

[a] In 2019, the Tri-Council of Cherokee tribes declared a state of emergency for the language due to the threat of it going extinct, and called for the enhancement of revitalization programs.

[14] After the intended federal dissolution of the Old Cherokee Nation under the Dawes Commission and allotments, Native American land claims in Indian Territory were extinguished and Oklahoma was admitted as a state.

[17] In the late 1940s, the United Keetoowah Band's claim to recognition as a tribe was probed according to criteria influenced by John Collier, who led the Bureau of Indian Affairs, and Felix S. Cohen.

Writer D'Arcy McNickle argued that the Cherokee Nation no longer existed in any form except to sign over Indian lands.

He suggested that the UKB be granted federal acknowledgment based on its authenticity and connection to the traditional ways, including maintenance of the language and ceremonies.

[20] Beginning in the 1970s, the UKB made some people honorary, adopted and associate members, to recognize their services to the nation.

Given the problems in the 21st century of persons trying to gain benefits by claiming distant Cherokee or UKB ancestry, the tribe no longer practices honorary membership.

[21] In the late 20th century, several tribes began to develop gaming facilities on their own sovereign or trust lands, and in consultation with affected states.

The State of Oklahoma has sued the UKB in federal court for operating what it describes as illegal gaming facilities, as they are not on Bureau of Indian Affairs-approved tribal trust lands.

[23] The Cherokee Nation said the UKB had sued to demand cession of tribal land allotments to them in order to build casinos.

[24] In June 2004, the UKB requested that the BIA take into trust land which the tribe owned on a fee basis, a 76-acre (31 ha) Community Services Parcel.