By late September 1864, Grant had been grinding at Petersburg for more than three months. His Fifth Offensive aimed to stretch Robert E. Lee's already-thin lines until something tore. On September 30, Union infantry under Warren and Parke seized ground around Peebles' Farm but failed to reach their real target, the Boydton Plank Road, Lee's last reliable supply route from the south. The Confederates planned a counterstroke. A. P. Hill, Henry Heth, and cavalry chief Wade Hampton looked at the Union right and saw what looked like a vulnerable flank. Meanwhile, General Meade pulled David Gregg's cavalry back from an exposed forward position to the Vaughan Road junction, worried about exactly the kind of attack Hampton was preparing.

The first contact came at night, and it was a fiasco. Brigadier General John Dunovant, a South Carolinian commanding the Confederate cavalry brigade in front, did not believe there was any real Union force on the road. He rode at the head of his column himself. When his men bumped into Henry Davies's Union troopers near Armstrong's house, Dunovant assumed he had found Confederate pickets and sent an aide forward to clear the way. The Union soldiers took the aide prisoner. In the confused firing that followed, both sides pulled back and Dunovant, embarrassed at being surprised, returned to his lines. The morning would offer him a chance to redeem himself, and he would take it.

By midmorning, Confederate brigades under Pierce Young and Matthew Butler had swept onto the Vaughan Road positions Gregg had just vacated. Gregg came back hard at 10:45 a.m. and drove them off. From then until late afternoon, the fight surged across McDowell's Farm and the adjacent Wilkinson's Farm. Carbine smoke hung low in the rain. Confederate Colonel James Lucius Davis got behind part of Davies's line with two Virginia regiments and captured forty-six Union prisoners. Wade Hampton himself rode forward with reinforcements but was slowed by the storm. A planned pincer movement on the Union flank dissolved when two Confederate columns blundered into each other in the wet woods and nearly opened fire on each other.

Hampton's officers debated whether to flank the Union position or assault it head-on. Dunovant, still smarting from the night before, pushed for the frontal charge. He was a man with something to prove. Earlier in the war, drinking had cost him his command of a regular Confederate regiment, and he had clawed his way back to brigade command. Whether ambition or judgment drove him now is impossible to say, but he led the assault himself. He was struck in the chest by a bullet and was probably dead before he hit the ground. Sergeant James T. Clancy of the 1st New Jersey Cavalry was credited with the shot. When Hampton's medical director, John B. Fontaine, rode forward to help, a shell killed him too. Demoralized, the Confederates pulled back.

The arithmetic of the day was modest. About 130 Confederate casualties, about 90 Union, nearly half of those Federals taken prisoner during Davis's earlier flanking move. Three Union artillery pieces broke up the final Confederate attacks at nightfall. President Andrew Johnson awarded Clancy the Medal of Honor on July 3, 1865. But Lee saw the larger shape of it. Two days after the fighting, he wrote to Hampton warning that if the Union could not be stopped from extending westward, it would eventually reach the Appomattox River and sever the Confederacy from the south. That is exactly what happened, six months later, on the road to Appomattox Court House.