Wilbur Rakestraw, from Dallas, Ga., was another driver from a family of racers. Rakestraw was a Ford loyalist, and raced his number 999 (in honor of Henry Ford’s first race car, piloted by Barney Oldfield) across the south. Rakestraw raced with the Southern Racing Enterprises organization all over the south. Rakestraw competed in 30 Cup events between 1956 and 1961, picking up one top five finish at Columbia, SC., and recording six top ten finishes. Among those starts were the first three Daytona 500s, in 1959, 1960, and 1961. His best finish in that event was a 22nd in 1959.
Rakestraw also competed in several NASCAR Convertible series events in 1958 and 1959. In 1958, Rakestraw competed in seven Convertible races, picking up three top fives and four top tens.
Rakestraw retired from driving after 1961.