Kenseth and the No. 17 Reiser Racing team were hired for several Cup Series races in 1999 by Roush Racing. In 2000, Roush hired the No. 17 team full-time for Cup Series racing with a sponsorship from DeWalt. Kenseth beat out Dale Earnhardt Jr to win the Raybestos Rookie of the Year. He won the Coca Cola 500 at Charlotte, and is the only rookie to win the famed 600 mile event. He went on to finish 14th in points with four Top 5s and 11 Top 10s.