The Battle of Sikeston was a battle fought between the Cherokee Indians and the Spanish Army near present-day Sikeston, Missouri in the winter of 1796.
In 1796, shortly after the Cherokee warband in Florida had captured St. Augustine from the Spanish, the Cherokee warchief Menawa led a series of raids on Upper Louisiana, a sparsely populated colony of the Spanish Empire which was garrisoned by a mere 200 soldiers based at Fort de Chartres. This Spanish garrison repelled two Sioux warbands near present-day Kennett, Missouri in the summer of 1796 before beginning to embark on the northbound return trip to Fort de Chartres. Sensing an opportunity to slay a large number of colonizers, Menawa led his warband south from Fontanet (which he had just raided) to attack the Spanish near the banks of the Mississippi River.
The Cherokee warband faced the 25 remaining soldiers of Spain's 5th Regiment of Foot and the 56 survivors of the 4th Regiment of Foot, as well as a dragoon detachment and two artillery batteries. The Spanish artillery pounded the Cherokee warriors, and the dragoons attempted to charge the Cherokee lancers on the right flank of the Cherokee force, only for Menawa to lead his bodyguards in a flank attack against the dragoons in conjunction with the lancers. The dragoons were massacred to a man, and the Cherokee cavalry on both flanks proceeded to charge the Spanish artillery batteries on both flanks as the Cherokee bowmen and musketeers closed in for combat with the Spanish regulars. The Spanish force quickly fell into a panic and routed, only for the Cherokee to ruthlessly pursue them and slaughter every last Spanish soldier. This left Fort de Chartres defenseless, and the Sioux occupied the vacant fort before the Cherokee could do so.
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