finishing in 32nd position. Shepherd last finished a Cup race in 1999. Shepherd also ran the full race at the summer Daytona race, finishing in 33rd place. Shepherd qualified for 19 races that year. Shepherd started his 500th Cup start at the Siemens 300 at the New Hampshire International Speedway. He qualified in 41st position and finished in 40th place after running 192 of the 300 laps. He finished 42nd in the final points standings. As Shepherd and his team received almost no money from sponsors whatsoever, they had to cut back on their 2005 schedule. Shepherd attempted to qualify for the 2005 Daytona 500 but missed the race after he was caught up in a wreck during the Gatorade Duels. This was a big blow to Shepherd's season as he needed the prize money to compete in all the races. Shepherd qualified for the next race he entered at Las Vegas. This was a much-needed break as his team needed the prize money to keep racing. Shepherd eventually managed to qualify for four of the 21 races he entered that season. He finished 63rd in the 2005 points standings. Shepherd's struggles continued in 2006. His team had to cut on their schedule and only entered 15 races that year. Shepherd failed to qualify for the first 9 races he entered in 2006. He made his first race of the year at the Chevy Rock & Roll 400, where he finished 43rd. The following week, he qualified for the Sylvania 300 and finished 42nd. Shepherd failed to make any additional races for the rest of the year. He finished 66th in the final points standings. Shepherd shut down his cup team after the season and moved to the Busch Series for 2007. Oldest driver to start Sprint Cup race Shepherd ran the Camping World RV Sales 301 at New Hampshire Motor Speedway for Brian Keselowski Motorsports, his first Sprint Cup race since 2006, becoming the oldest driver to race in the Sprint Cup at an age of 71 years, nine months and two days, and breaking the previous record held by Jim Fitzgerald, who ran at Riverside International Raceway in 1987 at age 65. Shepherd started 41st and finished in the same spot in a start-and-park effort, completing 92 of 301 laps. Shepherd attempted to make the 2014 Daytona 500 in the No. 93 for BK Racing in collaboration with