1982, driving the No. 98 Buick. Although Shepherd did not win a race that season, he scored six top-five finishes with a best finish of third at Bristol early in the season. Shepherd also won the pole at Nashville and Atlanta, respectively, but retired from both those races with engine troubles. Shepherd finished tenth in points that season with a total of thirteen top-ten finishes. Shepherd started the 1983 season without a full-time ride. He tried to qualify for the Daytona 500 driving for Bud Reeder; however, he failed to make the race. Shepherd then drove the Richmond 400 for Wayne Beahr but did not finish the race. Shepherd returned to Cecil Gordon for the TranSouth 500 and later drove the Virginia National Bank 500 for Emanuel Zervakis. After that race, Shepherd drove for Jim Stacy's team for the rest of the season. Shepherd scored thirteen top-ten finishes during the rest of the season, with a best finish of second at Firecracker 400. His abbreviated season dropped Shepherd to twentieth in the final points standings. Going from ride to ride For the next couple of years, Shepherd did not have a full-time ride and practically picked up whatever he could find. Shepherd started off his 1984 season at Richmond driving the No. 2 Buick for Robert Harrington. Shepherd drove two races for Charlie Henderson early in the season. He also drove four races for Dick Bahre his team, with a best finish of seventeenth at the 1984 World 600. Shepherd made one start for Phil Barkdoll at Michigan finishing the race in the 22nd position. After driving the No. 6 Buick for D. K. Ulrich and the No. 52 Chevy for Jimmy Means, Shepherd drove six races for Roger Hamby. Shepherd had two top twenty finished for Hamby, with a best finish of twelfth at Richmond. Shepherd made another start for Ulrich at Charlotte, before rounding off the season driving the No. 98 Chevy for Ron Benfield. Shepherd scored his only top ten finish that season at Rockingham, finishing in sixth position. Shepherd finished his first Daytona 500 in 1985, driving the No. 67 Chrysler for Buddy Arrington. Shepherd spent the rest of the season going from ride to ride. He returned to the team of Dick Bahre, driving the No. 23 Chevy at Rockingham. He also made a start for Petty Enterprises at the TranSouth 500. Shepherd fielded his