The Second Battle of Winchester took place as part of the Confederate invasion of the North led by General Robert E. Lee during the Gettysburg Campaign. Winchester, Virginia, had strategic importance due to its location within the Shenandoah Valley, serving as a logistical center and key entry point for movements into northern territories. General Lee aimed to expel Union forces from the area to secure the valley and facilitate his continued advance into Pennsylvania.

On June 14, 1863, General Robert H. Milroy commanded the Union garrison stationed in Winchester. Anticipating a possible Confederate advance, Milroy fortified his position; however, he underestimated the strength and skill of Lee's forces. The Confederate army, comprising General Richard Ewell’s corps, initiated a multi-pronged attack, using their numerical superiority and tactical prowess. By leveraging a surprise assault during the early morning, they surrounded Milroy’s troops and cut off their escape routes.

As the fighting intensified, Union forces faced fierce resistance and coordination from the Confederate troops. Unable to hold their lines against determined advances, Milroy’s forces were ultimately routed. Many Union soldiers were captured, while others fled in a disorganized retreat, significantly weakening Union control in the region and bolstering Confederate morale as Lee’s army continued its campaign northward.