2002
In his first qualifying attempt of his first full season with Hendrick Motorsports, Jimmie took the pole for the Daytona 500.

2001
Qualified 30th and finished 25th on the lead lap of the Pennzoil Freedom 400 at Homestead Miami Speedway on Nov. 11. Qualified 15th and finished 39th in the UAW-GM Quality 500 on Oct. 7 at Lowe's Motor Speedway - his first NASCAR Winston Cup Series appearance. Posted his first career NASCAR Busch Series win at the inaugural Hills Brothers Coffee 300 at Chicagoland Speedway.

2000
Finished 10th in the Busch Series point standings and third in the battle for Rookie of the Year. Best finish of sixth (three times) at South Boston Speedway (6/10), Michigan International Speedway (8/15), and Homestead Miami Speedway (11/11). Recorded best Busch Series start (fourth) at Darlington Raceway (9/2).

1999
Ran five Busch Series races - The Milwaukee Mile, North Carolina Speedway, Memphis Motorsports Park, Phoenix International Raceway and Homestead Miami Speedway. Earned a seventh-place finish in the first Busch Series start at The Milwaukee Mile (7/4). Finished third in the American Speed Association's (ASA) national championship point race. Captured ASA wins at Memphis Motorsports Park (6/12) and Orange County Speedway (10/12).

1998
Ran three Busch Series races - Indianapolis Raceway Park, Gateway International Raceway, and Homestead Miami Speedway. Finished fourth in the ASA national championship point race during his first full season. Named ASA Pat Schauer Memorial Rookie of the Year.