Battle of Opequon The Battle of Opequon , more commonly known as the Third Battle of Winchester , was fought in Winchester , Virginia , on September 19 , 1864 , during the Valley Campaigns of 1864 in the American Civil War . As Confederate Lt . Gen . Jubal A . Early raided the B & O Railroad at Martinsburg , WV , Union Maj . Gen . Philip H . Sheridan advanced toward Winchester along the Berryville Pike with the VI Corps and XIX Corps , crossing Opequon Creek . The Union advance was delayed long enough for Early to concentrate his forces to meet the main assault , which continued for several hours . Casualties were very heavy . The Confederate line was gradually driven back toward the town . Mid - afternoon , the VIII Corps and the cavalry turned the Confederate left flank . Early ordered a general retreat . Because of its size , intensity , serious casualties among the general officer s on both sides , and its result , many historians consider this the most important conflict of the Shenandoah Valley . Background . Sheridan was given command of the Army of the Shenandoah and sent to the Shenandoah Valley to deal with Early ' s Confederate threat . For much of the early fall of 1864 , Sheridan and Early had cautiously engaged in minor skirmishes while each side tested the other ' s strength . Early mistook this limited action to mean that Sheridan was afraid to fight , and he left his army spread out from Martinsburg to Winchester . Sheridan learned of Early ' s dispersed forces and immediately struck out after Winchester , the location of two previous major engagements during the war , both Confederate victories . Battle . Early quickly gathered his army back together at Winchester just in time to meet Sheridan ' s attack on September 19 . The Union forces coming in from the east had to march on the narrow road through Berryville Canyon , which soon got clogged up with supply wagons and troops , delaying the attack . This delay allowed Early to further strengthen his lines . Maj . Gen . John B . Gordon ' s division arrived from the north and took up position on the Confederate left . By noon Sheridan ' s troops had reached the field and he ordered a frontal attack along Early ' s lines . Maj . Gen . Horatio G . Wright ' s Union VI Corps on the left flank halted when faced with well entrenched Confederates on a hilltop supported by artillery . The XIX Corps , under Maj . Gen . William H . Emory , to the north of the VI Corps , drove Gordon ' s division through some woods , but when the Federals continued pursuing the Confederates through they were cut down by artillery as they entered the clearing on the far side . The VI Corps resumed its advance and began driving back the Confederate right flank , but the VI and XIX Corps were slowly moving apart from each other and a gap appeared between them . Brig . Gen . David A . Russell ' s division was rushed forward to plug the gap . Russell was hit in the chest , but continued moving his division forward . The brigade of Brig . Gen . Emory Upton reached the gap , but was too late — the Confederates had already launched a counterattack through the gap . Upton placed his men in line of battle and charged . Leading the charge was a young colonel named Ranald S . Mackenzie , commanding the 2nd Connecticut Heavy Artillery regiment , serving as infantry . Russell received a second bullet and fell mortally wounded . Upton assumed command of the division and a lull came over the battlefield . At this point Sheridan called the battle a " splendid victory " , but had no intentions of stopping the fight just yet . Sheridan sent the VIII Corps under Brig . Gen . George Crook to find the Confederate left flank . Meanwhile , cavalry units under Brig . Gen . James H . Wilson were swinging around the Confederate right flank . With the three corps in line , Sheridan ordered them all forward . This new advance did not start well . Crook ' s troops had to march through a swamp and the XIX Corps was not advancing at all . General Upton was struggling to persuade the XIX Corps units on his flank to move forward with his own division when an artillery shot tore off a chunk of his thigh . The surgeon was able to stop the bleeding and Upton ordered a stretcher brought forward from which he directed his troops for the rest of the battle . Finally the Confederate lines began to give way . Sheridan , so excited by the imminent victory , rode along the lines waving his hat and shouting . Late in the day , two divisions of Union cavalry arrived from the north and came thundering into the Confederate left flank . The division of Brig . Gen . Wesley Merritt crushed the Confederate works while the division of Brig . Gen . William W . Averell swung around the flank . The Confederate army was in full retreat . Caught in the retreat were the wives of several Confederate generals staying in Winchester . John B . Gordon was forced to leave his wife behind in attempts to keep his troops intact , believing she would become a prisoner of the Union army . She did , however , manage to escape in time . Aftermath . The Battle of Opequon marked a turning point in the Shenandoah Valley in favor of the North . Early ' s army for the most part remained intact but suffered further defeats at Fisher ' s Hill and Tom ' s Brook . Exactly a month later , the Valley Campaigns came to a close after Early ' s defeat at the Battle of Cedar Creek . Victory in the Valley , along with other Union victories in the fall of 1864 , helped win re - election for Abraham Lincoln . The battle was particularly damaging due to the number of casualties among key commanders . In the Union army , Brig . Gen . David A . Russell was killed and Brig . Gens . Emory Upton , George H . Chapman , and John B . McIntosh were seriously wounded . Confederate Maj . Gen . Robert E . Rodes was killed and Maj . Gen . Fitzhugh Lee , Brig . Gens . William Terry , Archibald Godwin , and Col . William Wharton were wounded . Also among the Confederate dead was Col . George S . Patton , Sr . His grandson and namesake would become the famous U . S . general of World War II , George S . Patton , Jr . Medals of Honor . During the Battle of Opequon , fourteen Union enlisted men and one officer received the Medal of Honor for their actions . Preservation . Most of the preservation effort at the Opequon Battlefield has been privately oriented . The Civil War Trust has preserved 222 acres of the 567 - acre battlefield . The most recent acquisition was made in 2009 by the Shenandoah Valley Battlefields Foundation , with participation by the Civil War Trust and the Virginia Land Conservation Foundation . At that time , these preservation groups purchased a 209 - acre parcel known as the " Huntsberry Farm " tract , named for a family who lived on the land at the time of the battle , for $ 3 . 35 million . The Shenandoah Valley Battlefields Foundation is presently engaged in restoring the battlefield , focusing first on the key battle area south of Redbud Run . Restoration and interpretation of this area is underway , focusing on the infamous 30 - acre Middle Field , in time for the 150th Anniversary of the battle in September , 2014 .