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The Battle of San Marcos de Apalache occurred in the winter of 1788 when the Cherokee war chief Ishtakhaba's raiding warband was brought to battle by the Spanish Army near the Spanish fort of San Marcos de Apalache (St. Marks) in Spanish Florida. The Cherokee defeated the Spanish and inflicted heavy losses, forcing the Spanish force to retreat to St. Augustine.

Following the European reoccupation of New Orleans, Ishtakhaba's Cherokee warband moved east to terrorize the Florida Panhandle, burning Pensacola, Wewahitchka, Osceola, and St. Marks in the process. The Native American warriors encamped near St. Marks to rest from their raids, tempting the Spanish colonel Nazario Valdez into leading his 330-strong garrison of St. Augustine to attack the 585-strong Cherokee warband on the outskirts of St. Marks. In the ensuing battle, the Cherokee warband split up into separate units to attack the 6th Regiment of Horse, 5th Regiment of Militia, 6th Regiment of Foot, and 5th Regiment of Horse. The Spanish cavalry found themselves being charged, and the provincial horsemen were routed with heavy losses. The Spanish line infantry initially held off the Cherokee warriors with their bayonets, but they were soon swamped by superior numbers. Valdez was killed, and his soldiers began to rout. The Cherokee cavalry pursued the fleeing Spaniards, butchering several of them before they could make it to safety. The remnants of the Spanish army withdrew to the safety of St. Augustine, while the Cherokee returned to razing the Florida Panhandle over the next several years, vainly attempting to lure out the Spanish garrison once again.

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