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Thursday, November 7, Col. Joshua W. Sill started the northern prong of the Big Sandy expedition toward John's Creek. From there he was to veer south for about forty miles and gain the rear of the enemy at Pikeville. The following morning, Nelson took the main column of 3,600 men toward Pikeville on the Old State Road (Rt. 460). Heavy rain fell in torrents as they neared Ivy Mountain, a hogback, 1,000-foot hill about 0.5 miles long. The West Levisa Fork of the Big Sandy River restricted movement on the right the seven-foot wide path and knee-deep mud forced the artillery to unlimber their guns and rig them so they could follow the infantry forward in a single file. About 15 miles west of Pikeville, the advance guard disappeared in the elbow of the path as it turned down toward the crossing at Ivy Creek. Directly to their front, there were 250 Confederates some 100 feet up the hill and hidden behind rocks, trees, and bushes. About 1:00 p.m., that hillside exploded with blue smoke from the doubled-barreled shotguns and old muskets carried by the Confederates. In the next instant, four Union soldiers were dead and another 13 lay on the ground wounded. Nelson rushed forward with his saber drawn, climbed up on a conspicuously located rock, and told his men "that if the Rebels could not hit him they could not hit any of them." He ordered the 2nd Ohio Infantry and 21st Ohio Infantry to push up side of the mountain and flank the enemy position from the north. At the same, Nelson had two light artillery pieces take a position near mouth of Ivy Creek and West Levisa Fork and fire directly into the enemy breastworks.
About 2:20 p.m., the 21st Ohio Infantry arrived at the top of hill. The rolled large boulders down on the Confederates who ran off in every direction. One half-hour later, Captain May had his men felling trees and burning bridges to retard pursuit. The Battle of Ivy Mountain (Ivy Narrows) was a clear victory for the Union force under Nelson who had gained full control of the field at a loss of six killed and 24 wounded. The opposing Confederates had 10 dead, 15 wounded, and 50 missing or taken prisoner. Nelson ended the pursuit beyond a burned bridge at Coldwater Creek and near the home of Unionist Lindsay Layne. Williams continued on to Pikeville where he posted a rear guard of 400 men to cover a withdrawal to Pound Gap with the remainder of his force. At 3:00 a.m. Saturday, November 9, Nelson had his troops back in pursuit. Terrible road conditions retarded movement and by nightfall, he remained 5 miles (8.0 km) from Pikeville. Early Sunday, November 10, Nelson had come to within several miles of the objective when a detachment from Joshua Sill's northern prong rode forward to advise they had secured the town at 4:00 p.m. Saturday.
In Pound Gap, Colonel Williams reported that Nelson had dispersed an "unorganized and half-armed, barefooted squad" that lacked everything, but the will to fight. The Cincinnati Commercial noted that Nelson had shown how "troops could be moved across unforgiving terrain without adequate transportation." That determination had truly surprised Williams who believed that Nelson would continue into Virginia with the intent of destroying the Virginia & Tennessee Railroad, a line that connected the Confederate capital at Richmond, Virginia with the Memphis, Tennessee and the Mississippi Valley at Knoxville. In the first accounts of the fighting at Ivy Mountain, Northern news correspondents grossly misrepresented events because their Northern audience wanted a quick conclusion to the war. Those mistakes led the Cincinnati Gazette to conclude that while a great victory had been attained, the "campaign in Eastern Kentucky has no more permanent effect than the passage of a showman's caravan. Five hundred rebel guerrilla cavalry will undo in a week the ornamental work . . . done at so great an expenditure of money and of most precious time." The latter issues were of great concern and the reason why Brig. Gen. Don Carlos Buell replaced Brig. Gen. William T. Sherman in Louisville. Nelson received orders to report there and his brigade followed on Sunday afternoon, November 24. As predicted, the Confederates returned and that brought Col. James A. Garfield into the region to resume the unfinished task of subduing them.