Robert A. Oakes was born around 1827. Confederates conscripted him in January 1863, and he mustered in as a private in the Ashby Virginia Horse Artillery in February 1863. According to his service records, he was 5 feet, 9 inches tall, with dark hair and dark eyes. The regiment took part in the Gettysburg campaign. Union forces captured him near Culpeper, Virginia, on September 13, 1863. He was imprisoned at Point Lookout, Maryland, until August 1864, when Union officials transferred him to Elmira, New York. He received a parole on February 25, 1865, and he eventually rejoined the Confederate army. He was paroled again in Staunton, Virginia, on May 15, 1865. He died sometime after the war.

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