Often identified as one of the Confederate army's great lost opportunities, this battle was the next to last of the Seven Days battles. With the Union army in full retreat toward the James River in the face of Lee’s offensive, the Southern army set its sights on the critical intersection at Riddle's Shop, often called Glendale and sometimes referred to as Charles City Crossroads. Most of the Union army would have to funnel through that bottleneck on its way to the river.
Seven Union infantry divisions deployed across several miles to guard the intersection. Four separate Confederate columns angled toward the crossroads. Northeast of the crossroads, at White Oak Swamp, 30,000 men led by Confederate general “Stonewall” Jackson made no progress against blue-clad divisions under generals Smith and Richardson. Two other Southern columns, commanded by Benjamin Huger and Theophilus Holmes, met substantial resistance and failed to threaten the Union position. The fourth column, which included the troops of generals A. P. Hill and James Longstreet, struck George McCall's Pennsylvania Reserve division west of Glendale on either side of the Long Bridge Road. In the bitter fighting—some of it with bayonets and clubbed rifles—the Confederates captured more than a dozen cannon and were able to push to the edge of the old Frayser Farm, within sight of the road leading south from the intersection to the James River. But they could go no farther. The intersection remained open, and the Union army retreated safely on the night of the 30th.