As James Blunt's First Division of the Army of the Frontier massed before Confederate artillery at the Cane Hill Cemetery, General John Marmaduke ordered J.O. Shelby's Rebels to fall back through Boonsboro. As the Confederates withdrew, Captain Henry Hopkins of the Second Kansas Cavalry placed his Trophy Battery on high ground and opened fire, hitting the Cane Hill College building. Union troops advanced but were checked by cannon fire from Charles Carroll's Arkansas Cavalry on high ground east of Jordan Creek, after which Marmaduke's army began a hurried retreat toward Cove Creek. Cane Hill College, chartered in 1852 as one of Arkansas's earliest institutions of higher education, occupied a two-story wood-frame building constructed in 1854, closed with the outbreak of the Civil War in 1861, and that structure was burned by Kansas cavalrymen in 1864. A new wood-frame building went up in 1868 and served until it burned in 1885, and the present brick building was constructed in 1886 before financial decline forced the college to close in 1891, after which the building served as a public school.