By midmorning on April 1, Sheridan's men had located the entrenchments that Pickett's men had thrown up along White Oak Road at Five Forks. In addition to the cavalry and infantry that manned the mile-and-three quarters line, the Confederates had also posted cannon at a few points with a field of fire.
Sheridan's men spread out to develope the extent of the position, and their scouting reports erroneously placed the enemy's left flank much farther east than it was.
Sheridan formulated a simple battle plan. He would mass all of Warren's infantry against the enemy's left, and while his troopers pressed all along the front, the foot soldiers would turn the flank. The roads were muddy and the terrain a tangle of underbrush, so it took Warren's men until almost 4:00 p.m. to form where Sheridan wanted them. The restless, combative cavalrymen attributed these delays to Warren's lack of leadership. Finally, between 4:15 and 4:30, the attack commenced.
Just about every element in Sheridan's plan failed to perform as intended. His cavalrymen were unable to mount any serious advance against the White Oak Road line and were, for the most part, spectators to the combat that did take place. The infantry advance also faced serious problems. As dictated by Sheridan, Warren's corps advanced in a two division front with the third following on the right as a reserve. Sheridan intended for the right front division (Brevet Major General Samual W. Crawford commanding) to strike the angle of the enemy's works, with the left front (under Brevet Major General Romeyn B. Ayres) taking the line headon. But the faulty cavalry reconnaissance now bedeviled the execution of these instructions. The real flank was well west of where Sheridan thought it to be, so much so that General Crawford's division missed it completely as it moved forward, and Ayers's men took fire from their left as they brushed past it.
Ayers needed about fifteen minutes to reorient his units and to mount an attack toward the flank. This maneuver broke contact with Crawford, who continued to advance as ordered and was soon lost to sight in the heavy thickets. The reserve following Crawford, Brevet Major Charles Griffin's division, halted while its commander sorted things out. Warren, trying to hold a central position, sent all of his aides galloping off to reorient his errant divisions, and, when that failed, he rode out to take command himself. Sheridan, riding with Ayers's advance, led the charge that breasted and captured the left flank of Pickett's White Oak Road line.
Helping the Federals immeasurably was a command paralysis on the Confederate side. When most of the day had passed with no sign of an attack, both Pickett and Fitzhugh Lee rode off to a shad bake with Major General Thomas L. Rosser, whose reserve cavalry was camped on the north side of Hatcher's Run. The two officers neglected to notify their next in command that they were absent, so there was a fatal break in the Confederate chain of command. With no one in overall control, southern soldiers fought the blue waves in isolated pockets of resistance. In a crowing piece of irony, atmospheric conditions so muffled the sound of battle that neither Pickett or Fitzhugh Lee knew that anything was happening until it was far too late to reverse the situation.
After Ayers's men stormed and overran the return, dazed Confederates tried to organize a new defensive line to face them, but Griffin moved in on Ayers right and beat them down. Then Crawford appeared, coming down from the north, directed there by General Warren. Now Sheridan's cavalry came alive and swept around the Confederate right, only to be caught up in a wild melee that allowed many of the Rebel infantrymen to escape.
Nevertheless, it was a stunning victory. Of the 9,200 men under Pickett and Lee, nearly a third were killed, captured, or wounded, at a loss to Union arms of slightly more than 800. The way was now wide open to the South Side Railroad, and Robert E. Lee's best escape route was closed.