Driving a car owned by his father, George Elliott, Elliott made his first Winston Cup Series start at Rockingham in 1976. He qualified 34th in a field of 36 cars; Elliott only lasted 32 laps that day before the oil pump failed in his Ford Torino. Elliott toiled for five years in the Winston Cup Series without corporate sponsorship, and along the way showed flashes that he could compete with the established veterans of the sport. In mid-1977, Elliott bought a Mercury Montego from Bobby Allison after his split from Penske Racing to replace the inferior Torino, and the move paid off. He soon earned his first Top 10 finish in the Southern 500 (10th), and his first top-5 finish 2 years later in the same race, finishing second to race winner (and Elliott's boyhood hero) David Pearson.