races and finished second 21 times. The Shepherd-Stewart combo moved to what was then the Winston Cup Series for the 1981 season. Winston Cup Series Early days Shepherd made his Winston Cup Series debut in 1970 at Hickory Motor Speedway, driving the No. 93 Chevy for Bill Flowers. He started tenth but finished nineteenth out of twenty-two cars due to rear-end failure. Shepherd made two more starts for Flowers that year but failed to finish in both of them. His best finish that year was a fourteenth place at Hickory. Shepherd would not return to the Cup Series until 1977, driving a Mercury for Jim Makar. He first attempted the Daytona 500 that year but he failed to make the race. Later that year Shepherd took his first top-ten finish at Dover International Speedway. He also ran two additional races at Charlotte Motor Speedway and Atlanta Motor Speedway. Shepherd stayed with Makar for the 1978 season, qualifying for his first Daytona 500. Shepherd started the race in 37th place but only finished 40th when his engine failed after only eight laps. He only ran one additional race that season, finishing twelfth at Charlotte. Shepherd only attempted the Daytona 500 with Makar in 1979, but failed to make the race. Full-time Cup Series switch Shepherd moved to the Winston Cup Series full-time in 1981, driving the No. 5 Pontiac for Cliff Stewart. They missed the first two races of the season, Riverside and the Daytona 500. Shepherd took pole position in his first race for Stewart at Richmond, finishing the race in fourth position. A few races later Shepherd won his first Winston Cup race at Martinsville. The win marked the first win for Pontiac in 18 years. Shepherd dominated the race and led a total of 203 laps. Shepherd left Stewart's team after the Talladega 500 after he had a falling out with his team. For the next race at Michigan Shepherd drove for Bud Reeder his team. Shepherd qualified in the fourteenth position but retired from the race after he crashed on lap twenty. For the next couple of races Shepherd drove for Cecil Gordon and his team, finishing in the top ten at North Wilkesboro and Charlotte. During the last part of the season, Shepherd also drove some races for Ron Benfield. Shepherd finished thirteenth in points with ten top-ten finishes. Shepherd moved to Benfield's team full-time in