To support the Meridian Campaign, Maj. Gen. William T. Sherman ordered Brig. Gen. Sooy Smith to leave Colliersville, Tennessee, west of Memphis & Ohio Railroad, then strike south through Okolona to unite with Sherman's force at Meridian on February 10th. Contrary to instructions to push ahead with a smaller force and maintain the schedule, Smith waited until the 11th, when he was joined by Col. George E. Waring and 2,000 cavalry reinforcements from Columbus, Kentucky. On the 11th, far behind schedule, Smith, 7,000 cavalry, 20 artillery pieces, and a pack and ambulance train left Colliersville, moving southwest for Pontotoc, with Brig. Gen. Benjamin H. Grierson, 2nd in command.
Burning corn and cotton, tearing up Memphis & Ohio Railroad track, Smith's column pushed aside 600 Mississippi militia under Col. Samuel Gholson and pressed south almost unimpeded. En route, the Federals attracted more than 1,000 slaves seeking protection and passage to freedom.
Maj. Gen. Nathan B. Forrest had a force of 2,500 cavalry scattered north of Meridian. After a week of raiding, Smith's troops made numerous contacts with Forrest's advance elements. On the 20th, Smith's main column skirmished with Forrest's men at Prairie Station, 15 miles north of West Point, and a Union flank column collided with a Confederate brigade under Col. Jeffery E. Forrest at Aberdeen, northeast of West Point along the west fork of the Tombigbee River. Daunted by Nathan Forrest's reputation, uncertain of the number of Confederate troops he faced, and wooried over the fate of the escaped slaves, Smith ordered his men to concentrate at Prairie Station, then rode for West Point at dawn on the 21st.
At 2:00 A.M. on the 21st, Jeffrey Forrest pulled his brigade from Aberdeen and rode southwest, intercepting Smith's column shortly after its dawn departure. Fighting and withdrawing steadily, he drew the Union force 4 miles south of West Point onto swampy ground with the Tombigbee River on its left, the Okitbbeha River on its right, and the Sakatonchee Creek on its front. At Maj. Gen. Forrest's order, Brig. Gen. James R. Chalmers' small division and Col. Robert A. McCulloch's brigade arrived on the south bank of the Sakatonchee and crossed at early morning to reinforce Jeffrey Forrest and bring on a general engagement.
Smith, rationalizing the raid's accomplishments and difficulties and believing the Confederate superior numbers, claimed the West Point confrontation was a trap set up for him by the Confederates and ordered a retreat to Tennessee. He designated his advance to form a rear guard, then ordered the bulk of his column to press north. The Union rear guard, though unnerved by the swampy conditions, were protected on their flanks by the Sakatonchee and the Tombigbee. They held the Confederates at the Okitbbeha crossing for 2 hours, then withdrew. Nathan Forrest arrived on the scene and ordered pursuit. This ended the engagements at West Point.
Through the rest of the 21st, Confederates skirmished with the Union column, sniping at one another for 25 miles and engagements in several minor clashes. At dawn on the 22nd, 4 miles south of Okolona, Confederate advance elements attacked Smith in an open area locally called "the prairie."
Additional Confederate units arriving on the field broke the Union lines in an enthusiastic charge, initiating an 11 mile running skirmish. Union troops twice tried to make a stand, first 1 mile, then 2 miles north of Okolona. After losing 6 artillery pieces in the retreat, Smith's men organized a defense in woodland hills and around buildings at the Ivey's Farm Plantation, 7 miles northwest of Okolona. A general Confederate charge was repulsed in which Jeffery Forrest was killed. A 2nd charge and a Confederate move on Smith's right flank and rear failed. Federals organized 2 countercharges. Nathan Forrest's men, fighting dismounted in the open, and in inferior numbers, miraculously repelled both. Federals broke off the engagement and continued a retreat to Pontotoc. Forrest, his men nearly out of ammunition, ordered a halt. This ended the engagement at Okolona. Mississippi militia picked up the pursuit and harassed the Federals to the Tennessee line. Smith's column arrived at Colliersville, Tennessee on the 26th.
For the fighting of the 20-22nd, Forrest reported a total of 144 casualties and did not give any specific count for the individual engagements. Similarly, Smith reported 700 casualties for his entire raid but did not give any clear count for West Point or Okolona. The majority of Union casualties are believed to have occured on the 20th.