On the morning of April 5, Sheridan sent Brigadier General Henry E. Davies's brigade of Major General George Crook's division to scout for Confederate movements beyond Amelia Court House near Paineville, or Paine's Cross Roads, about 5 miles (8.0 km) north of Amelia Springs. At Paineville, Davies found a headquarters wagon train guarded by Brigadier General Martin Gary's cavalry brigade. This was the wagon train that had left Richmond with provisions for Lee's army, including food and ammunition for Ewell's corps. Since it had followed a more circuitous route north of Genito Bridge on Paineville Road, it had only some cavalry escort. The train crossed to the south side of the Appomattox River by the Clemmentown Bridge.
As Davies's brigade slowly passed the resort at Amelia Springs, the wagon train with excess artillery and equipment started up the Paineville Road from Amelia Court House toward Paineville at the same time as the wagon train from Richmond headed south on that road toward Paineville. Local citizens began to spread out on horseback to warn the Confederates of the Union cavalry incursion.
Davies attacked the lead section of the wagon train, two companies of artillery, 4 miles (6.4 km) east of Paineville, and quickly rounded up 300 soldiers and as many African-American teamsters. The Union cavalrymen cut many horses and mules out of their traces, captured five new Armstrong guns and burned more than 100 wagons of provisions. Davies's troopers destroyed Major General Custis Lee's supplies including all the spare ammunition. Leading wagons from the train which left Amelia Court House, including Fitzhugh Lee's headquarters baggage, Robert E. Lee's headquarters wagons with many reports and some ambulances and medical supplies, also were caught by the Union raiders. Stragglers and sick soldiers finally gathered to stop the destruction.
Before Davies could return to Jetersville, his brigade was attacked near Amelia Springs by Brigadier General Martin Gary's cavalry brigade and a much larger force of Thomas L. Rosser's and Colonel Thomas T. Munford's divisions under Major General Fitzhugh Lee. Davies's force was driven back across Flat Creek. Acting as a rear guard, the 1st New Jersey Volunteer Cavalry Regiment held off the Confederate pursuers, allowing Davies's main column with prisoners and captured horses, mules and artillery to move past Amelia Springs. At Amelia Springs, the other brigades of Crook's division under Brigadier General J. Irvin Gregg and Colonel (Brevet Brigadier General) Charles H. Smith provided reinforcements, allowing Davies's force to reach Jetersville with their prisoners, guns and teams. Davies returned with his men to Amelia Springs to help defend against the Confederate cavalry attack.
Crook's cavalry division had casualties of 13 killed, 81 wounded and 72 missing and probably taken prisoner in three encounters during the day. Fitzhugh Lee said he counted 30 dead Union soldiers along the way. Davies captured 320 Confederate soldiers and 310 African-Americans whom he described as teamsters. He also captured 400 animals and 11 flags while destroying about 200 wagons. Confederate casualties were unreported but two Confederate captains are known to have been mortally wounded.
Having not been able to find much food in the Amelia Court House area and with the Union Army closing in, Lee started his army marching down the route of the Richmond and Danville Railroad toward Jetersville, Virginia at 1:00 p.m. on April 5.
Nearing Jetersville and hearing skirmish fire in front, Lee discovered that his route to Danville along the railroad was blocked at Jetersville by the fast-moving Union cavalry under Major General Philip Sheridan. Union infantry was reported by cavalry scouts to be nearby but in fact the V Corps had already reached Jetersville.
Lee decided his men were too spread out and it was too late in the day to attack the Union force at Jetersville. So the Confederates would have to march back up the Richmond and Danville Railroad to a road upon which to make another night march to Farmville. At Farmville, 23 miles (37 km) west on the South Side Railroad, Confederate Commissary General Isaac St. John told General Lee that he would have 80,000 rations waiting. From Farmville, Lee might be able to reach the Richmond and Danville at Keysville, Virginia if the Confederates could outpace the Union forces.
The Confederate march was held up before the troops could reach Amelia Springs because a bridge was out at Flat Creek which needed to be repaired to allow the passage of wagons and artillery. During the night, Union spies dressed in Confederate uniforms were captured with a message that showed the disposition of the Union forces.