In the lead-up to the Battle of Gettysburg in June 1863, the Second Winchester Battle played a pivotal role in determining troop movements and strategy. Confederate General Robert E. Lee ordered the Second Corps, led by Lt. Gen. Richard S. Ewell, to clear the lower Shenandoah Valley of Union forces. Ewell's troops executed a brilliantly coordinated series of maneuvers, ultimately surrounding and decisively defeating the Union garrison under Maj. Gen. Robert H. Milroy at Winchester, Virginia. The Union forces were caught off guard and, believing their positions to be stronger than they were, ended up being routed with significant losses.

The battle's outcome had broad implications. The victory at Second Winchester cleared the Shenandoah Valley of significant Union resistance, paving the way for Lee's second invasion of the North. Ewell's capture of Winchester yielded an immense haul of Union supplies, helping to provision the Confederate Army. The defeat sent shockwaves through the North, leading to calls for additional militia and fostering fears of a deep Confederate incursion into Union territory.

Aside from the tactical and strategic implications, the leadership displayed by the Confederate generals, particularly Jubal Early, was noteworthy. Their ability to coordinate and execute complex maneuvers showcased their prowess and solidified their reputations as formidable military leaders. This victory bolstered Confederate morale and set the stage for the subsequent Battle of Gettysburg, one of the most significant confrontations of the American Civil War.