In 1999, Barrett announced his intention to compete part-time in the Winston Cup Series, running for Rookie of the Year honors with PBH Motorsports, with plans to run full-time in 2000. During testing for General Motors at Daytona International Speedway, Barrett was the sixth-fastest driver with a speed of . However, he failed to qualify for the Daytona 500. Barrett worked out a late-season deal with Donleavy Racing to make eight race attempts in 1999. in 2000, he attempted the Budweiser Shootout qualifier for drivers who ran the fastest in 2nd-round-qualifying in 1999, but crashed on the first lap with Jimmy Spencer, Rick Mast and Kenny Wallace. He joined the Tri-Star Motorsports team for the 2000 Daytona 500.