Gray enlisted as a member of Major Joseph C. Morehead's partisan rangers on May 24, 1862, Memphis TN. After receiving an appointment to the U.S. Military Academy at West Point NY in 1845, Morehead served as an commissioned officer in the U.S. Army. In 1860 Morehead was an attorney living in Jackson MS.
After Morehead's capture near Hernando MS, June 17, 1862, I'm not at all sure what became of his command. It seems that officers in the Confederate War Department felt the same way. Records show that Drakeford Gray was transferred to Capt. Jo Desha's Company by special order on Nov. 1, 1862. Formerly an officer of the old 1st Kentucky Regiment, Desha organized this company at Cynthiana KY on Sept. 28, 1862. Apparently during the next few months this command served with Col. John C. Wickliffe's 9th Kentucky Regiment, Army of Tennessee.
Assigned to complete the regiment of Col. Hiram Hawkins after its reorganization for three years or the war, Desha's company became 3rd Company "I" of the 5th Kentucky Regiment on Aug. 22, 1863. Drakeford Gray was wounded during the fighting at Jonesboro GA, Sept. 1, 1864.
If someone else has a better handle on this situation (the Confederate version of "Who's on First"), I would be pleased to see it.