Following the stalemate at the Battle of Seven Pines on May 31 and June 1, 1862, McClellan's Army of the Potomac sat passively in their positions around the eastern outskirts of Richmond. The new commander of the Army of Northern Virginia, General Robert E. Lee, used the following three and a half weeks to reorganize his army, extend his defensive lines, and plan offensive operations against McClellan's larger army. McClellan received intelligence that Lee was prepared to move and that the arrival of Maj. Gen. Thomas J. "Stonewall" Jackson's force from the Shenandoah Valley was imminent.

McClellan decided to resume the offensive before Lee could. Anticipating Jackson's reinforcements marching from the north, he increased cavalry patrols on likely avenues of approach. He wanted to advance his siege artillery about a mile and a half closer to the city by taking the high ground on Nine Mile Road around Old Tavern. In preparation for that, he planned an attack on Oak Grove, south of Old Tavern and the Richmond and York River Railroad, which would position his men to attack Old Tavern from two directions. Known locally for a stand of tall oak trees, Oak Grove was the site of Maj. Gen. D.H. Hill's assault at Seven Pines on May 31 and had seen numerous clashes between pickets since that time.

The attack was planned to advance to the west, along the axis of the Williamsburg Road, in the direction of Richmond. Between the two armies was a small, dense forest, 1,200 yards (1,100 m) wide, bisected by the headwaters of White Oak Swamp. Two divisions of the III Corps were selected for the assault, commanded by Brig. Gens. Joseph Hooker and Philip Kearny. Facing them was the division of Confederate Maj. Gen. Benjamin Huger.

The Battle of Oak Grove took place on June 25, 1862, in Henrico County, Virginia, the first of the Seven Days Battles (Peninsula Campaign) of the American Civil War. Maj. Gen. George B. McClellan advanced his lines with the objective of bringing Richmond within range of his siege guns. Two Union divisions of the III Corps attacked across the headwaters of White Oak Swamp, but were repulsed by Maj. Gen. Benjamin Huger's Confederate division. McClellan, who was 3 miles (4.8 km) in the rear, initially telegraphed to call off the attack, but ordered another attack over the same ground when he arrived at the front. Darkness halted the fighting. Union troops gained only 600 yards (550 m), at a cost of over a thousand casualties on both sides.