From there the native of El Cajon, Calif., finished fourth in the 1998 ASA series standings, taking yet another rookie of the year award. In 1999, Jimmie took two ASA wins and moved up to third in the season standings. Jimmie also made his Busch Series debut in 1999, finishing seventh in his very first Busch Series start at the Milwaukee Mile. A year later, he finished 10th in the Busch Series standings with three sixth-place finishes.
He finally visited Victory Lane in the 2001 Busch Series, winning the inaugural Busch Series race at Chicagoland Speedway. Adding four top-five and eight top-10 finishes in 2001, Jimmie finished eighth in the series points standings before making his Cup debut in 2002. While he lost the Cup rookie of the year battle to Ryan Newman that year, Jimmie did make history by becoming the first rookie ever to lead the Cup standings on the way to a fifth-place point finish.
In 2004, Jimmie gained 2 places to be in 2nd place for the Chase to the Nextel Cup with his emotional win in the Bass Pro Shops MBNA 500, 1 week after losing 10 members of the Hendrick Motorsports family in a plane crash. This caps a 3 race winning streak where he currently trails point leader Kurt Busch by 59 points with 3 races left.
