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Gen. Joseph E. Johnston’s plan of attack for the morning of May 31, 1862, called for the divisions of Maj. Gen. James Longstreet and Brig Gen. William H. C. Whiting to advance along the Nine Mile Road, while the divisions of Maj. Gen. D. H. Hill and Maj. Gen. Benjamin Huger moved east along the Williamsburg Stage Road. Longstreet’s men followed the wrong approach roads in the pre-dawn darkness and instead followed Hill along the Williamsburg Road. Around 1:00 p.m. Hill attacked Union skirmishers and pushed through to a redoubt near the “twin houses” held by Brig. Gen. Silas Casey’s inexperienced division. Casey fell back and was supported by Brig. Gen. Phil Kearny’s division from the III Corps and Brig. Gen. Darius Couch’s IV Corps brigade. Longstreet fed in the brigade of Brig. Gen. R. H. Anderson to support Hill.

To the north, Brig. Gen. John Sedgwick’s II Corps division crossed the Chickahominy over Grapevine Bridge and arrived on the Union right. Around 4:30 p.m., Whiting attacked Sedgwick near the Adams family home, where Sedgwick held his position. As darkness fell, both sides brought up reinforcements to continue the fight the next day.

Early on June 1, the Confederates renewed their assaults. Brig. Gen. Israel Richardson’s II Corps division posted along the railroad was attacked by the brigades of Brig. Gens. Lewis Armistead and William Mahone from Maj. Gen. Benjamin Huger’s division. Richardson was supported by Brig. Gen. David Birney’s III Corps brigade and Brig. Gen. George Pickett supported Armistead and Mahone. Brig. Gen. Joseph Hooker’s III Corps division attacked Brig. Gen. R. H. Anderson’s division as the Confederates withdrew, ending the battle.