In 1999, he concentrated mainly on the Nationwide Series but also participated in five Sprint Cup events to get a feeler of that racing style. His best place finish was a tenth place finish at the Richmond race track in September that year. He had an extremely strong 2000 as he became the first rookie to win the Sprint All-Star Challenge. He was just 42 points behind Matt Kenseth in the race for the title of Rookie of the year. He won two races and had a 16th place finish in the series’ standings. He was getting accustomed to racing at the big stage and it was considered to be just a matter of time before he would win the entire thing.
In 2001, he came on stronger in a year that held a deep personal tragedy for Dale Jr. He lost his father at the Daytona race track on the 18th of February and when he returned there in July, he took his first win. His second win came after a tragedy that struck the entire country. After the September 11th attacks, he won at Dover and his final win that season was to come at Talladega, the venue for his father’s last career win. He finished the year in eighth place despite the tragedies that he had faced and proved that he was strong on the mental side of the game as well.
He dropped a bit in the rankings in the next year where he won just 2 races. He had 27 top-ten finishes though, out of which 11 were in the top-five. He started his own racing team, JR Motorsports as a means to race in the Nationwide Series and won his first Nationwide series race as driver/owner of the team.
He hammered home the point in 2003 when he finished an incredible third in the Sprint Cup Series. He won two races that season and for a majority of the season, was in the standings at second place. He posted 13 top-five finishes and 21 top-ten finishes. He was voted as the most popular driver and again became part of the only father and son duo who have been recipients of this award. He also entered three Nationwide Series races in 2003 and ended up with victories in all three.
His number of wins increased in 2004, to six wins, but his overall ranking reduced to the 5th in the Sprint Cup’s finalstandings. He took part in 4 restrictor plates races and became the only driver to post top-ten finishes in each of the four races that included two wins as well. He had a disappointing 2005 series wherein there were numerous changes in his team’s leadership and Dale Jr. just managed to finish the season in 19th place. He had just 7 top-five finishes and 13 top-ten finishes but got voted as the most popular driver for the third year in a row.
He got some of his previous form back in 2006 as he won one race, finished in the top-5 on ten races and had 17 top-ten finishes. After missing out on the Chase in the season before, he was back again for another season as he finished the season in 5th place.
2007 was his last season with his father’s racing team, Dale Earnhardt Inc. and he announced that he would be joining theHendrick Motorsports team for the ‘08 season. He finished the season in 16th place with seven top-five finishes and 12 top-10 finishes but no wins, his first full season where he didn’t manage to win a single race. Again, he was voted as the most popular driver for the fifth time in a row.
Dale Jr. has had an illustrious career, which still is pale compared to his father’s 7 championship wins. Although comparisons with his father will be inevitable, Dale Jr. will be looking to make his own landmarks and will be looking at 2008 as an opportunity to improve on his position in the rankings.