On October 17, 1864 Confederate General John B. Gordon arrived at Hupp's Hill and planed an attack. Gordon ruled out the possibility of a direct attack due to the strength of the Union position. Wharton’s division moved to Hupp's Hill at approximately 4:30 am on the morning of October 19th, with orders to support the main attack to the east. Once Wharton received word that Kershaw’s attack had opened, his division moved forward to Stickley Hill. During this, around the same time, Confederate Artillery Colonel Tom Carter arrived at Hupp's Hill and began firing on the Federals.
On top of Stickley Hill, George Custer was joined by Colonel Thomas C. Devin of the Merritts Calvary Division. Their efforts were direct their regiments movements against the retreating Confederates. In the middle of the Confederate retreat, a defensive position was attempting to be established on Hupp's Hill. Using blockades and spraying debris across Route 11 were a few of the defense tactics used. Although these tactics were used, the Federal Calvary pushed through.
As a result of, the First Division XIX Corps occupied Hupp's Hill on the evening of October 19. This is the division that dug that earthworks that are still visible today in the Hupps Hill Civil War Park.