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The Battle of Okolona took place on February 22, 1864, in Chickasaw County, Mississippi, between Confederate and Union forces during the American Civil War. Confederate cavalry, commanded by Maj. Gen. Nathan Bedford Forrest, faced over 7,000 cavalry under the command of Brig. Gen. William Sooy Smith and defeated them at Okolona, causing 100 casualties for the loss of 50.
Smith's force had been ordered to set off from Memphis, Tennessee, and rendezvous with the main Union army of 20,000 that was marching on Meridian, Mississippi, and was under the command of Maj. Gen. William Tecumseh Sherman. However, Smith disobeyed orders and delayed his march for ten days waiting on a unit that was ice bound in Kentucky. When he eventually left, he encountered the Confederate cavalry force on February 21, and on February 22 was engaged in a running battle across eleven miles with Forrest's forces. With Confederate reinforcements, Forrest routed Smith but did not pursue due to lack of ammunition, and Smith limped over the state line to Tennessee on February 26, where he was criticized for putting Sherman's Meridian Expedition in danger.