Fairplay was built in 1859 at New Albany, Ind., for service out of Vicksburg, Miss. She served as a Confederate transport on the Yazoo and other tributaries of the Mississippi. In August 1862 she was ordered out of the Yazoo to convey arms, munitions, and stores from Vicksburg to Milliken's Bend, thence up the Mississippi River for a load of corn which she safely delivered to the same landing. She transported arms from Vicks-burg to Milliken's Bend a second time, and had arrived with a third shipment on 18 August 1862 when she was surprised and captured with her cargo intact by a Federal gunboat fleet which had sailed from Helena, Ark. At that time, Fairplay was under command of Captain White, a citizen of Milliken's Bend. Her prize cargo was said to include 5,000 Enfield rifles and muskets; much ammunition and quartermaster stores.
Fairplay was armed with four 12-pounder howitzers and taken into the Federal Western Gunboat Flotilla which was transferred to the jurisdiction of the United States Navy on 1 October 1862 and redesignated the Mississippi Squadron. She spent the remainder of the Civil War on patrol as a Federal gunboat in the Cumberland, Tennessee, and Ohio Rivers. Fairplay was decommissioned at Mound City, Ill., on 9 August 1865 and sold on 17 August 1865.
