On May 9, the most powerful cavalry force ever seen in the Eastern Theater—over 10,000 troopers with 32 artillery pieces—rode to the southeast to move behind Lee's army. They had three goals: first, and most important, defeat Stuart, which Sheridan did; second, disrupt Lee's supply lines by destroying railroad tracks and supplies; third, threaten the Confederate capital in Richmond, which would distract Lee.

The Union cavalry column, which at times stretched for over 13 miles (21 km), reached the Confederate forward supply base at Beaver Dam Station that evening. The Confederate troops had been able to destroy many of the critical military supplies before the Union arrived, so Sheridan's men destroyed numerous railroad cars and six locomotives of the Virginia Central Railroad, destroyed telegraph wires, and rescued almost 400 Union soldiers who had been captured in the Battle of the Wilderness.

The Union cavalrymen suffered 625 casualties, but they captured 300 Confederate prisoners and recovered almost 400 Union prisoners. Sheridan disengaged his men and headed south toward Richmond. Although tempted to burst through the modest defenses to the north of the city, they continued south across the Chickahominy River to link up with Maj. Gen. Benjamin Butler's force on the James River. After resupplying with Butler, Sheridan's men returned to join Grant at Chesterfield Station on May 24. Sheridan's raid achieved a victory against a numerically inferior opponent at Yellow Tavern, but accomplished little overall. Their most significant achievement was killing Jeb Stuart, which deprived Robert E. Lee of his most experienced cavalry commander, but this came at the expense of a two-week period in which the Army of the Potomac had no direct cavalry coverage for screening or reconnaissance.