The Second Battle of Cynthiana, fought on June 11–12, 1864, began as a brilliant but costly success for Confederate Brigadier General John H. Morgan during his final raid into Kentucky. On the first day, Morgan’s 1,200 cavalrymen overwhelmed a small Union garrison by setting fire to the town to flush out defenders and subsequently trapping a second Union relief force at Keller’s Bridge. By nightfall, Morgan had secured a tactical victory and captured over 1,000 prisoners; however, the achievement left his men dangerously low on ammunition and exhausted from hours of continuous engagement.

Despite his dwindling supplies, Morgan chose to remain in Cynthiana rather than retreat, a decision that proved fatal to his command. At dawn on June 12, Union Brigadier General Stephen G. Burbridge launched a crushing counterattack with a superior force of 2,400 fresh troops and artillery. The Confederates were driven back into the town in a rout, resulting in heavy casualties and the permanent fracturing of Morgan’s force. This Union victory effectively ended Morgan’s career as a raider and signaled that Confederate partisans could no longer operate in the region with impunity.