December 5, 1862 – Federal Major General Ulysses S. Grant’s overland advance toward Vicksburg included a cavalry engagement in central Mississippi.
By the beginning of the month, Grant had established his main supply base at Holly Springs, along the Mississippi Central Railroad. Meanwhile, Lieutenant General John C. Pemberton’s Confederates had entrenched along the Tallahatchie River, north of Oxford.
Grant directed Colonel Theophilus L. Dickey to lead four cavalry regiments from XIII Corps to push the Confederates from their trenches and pursue them across the Tallahatchie toward Oxford. Grant’s remaining force began moving south out of Tennessee, along the Mississippi Central line. Skirmishing occurred north of Abbeville.
Assembling near the Tallahatchie River on the 2nd, Dickey’s troopers clashed with Major General Earl Van Dorn’s rear guard as it withdrew through the town and on through Oxford. Grant’s Federals soon occupied that town, and Grant directed Dickey to continue pursuing the enemy as far as possible.
Dickey split up his four regiments, but some accidentally met at Water Valley, below the Yocknapatalfa River, where they met heavy Confederate resistance on the 4th. Unaware of the enemy’s strength, Dickey decided to press on toward Coffeeville the next day.
The Federal troopers crossed the Otuckalofa River south of Water Valley on the morning of the 5th and moved down the Coffeeville road. Encountering Confederate skirmishers around 2 p.m., the Federals deployed in battle formation while firing their two cannon. The Confederates, consisting of Van Dorn’s rear guard, answered with six guns of their own and advanced to meet the enemy.
Dickey ordered a withdrawal, with his Federals stopping occasionally to exchange fire with the pursuing Confederates. The chase ended that evening, as night fell and the Federals took up strong defensive positions. The Federals sustained 116 casualties (10 killed, 63 wounded, and 43 captured), and the Confederates lost 50 (seven killed and 43 wounded).
The Federals returned to Oxford, but their overall expedition from the Tallahatchie River to Coffeeville resulted in the capture of 750 Confederates, 200 horses, four supply wagons, and $7,000 in Confederate currency. Federal forces continued probing southward this month.
Fredriksen, John C., Civil War Almanac (New York: Checkmark Books, 2007), p. 234-35; Stanchak, John E., Historical Times Illustrated Encyclopedia of the Civil War (New York: Harper & Row, 1986, Patricia L. Faust ed.), p. 148-49, 781