Sadler struggled in 2008, garnering only 2 top fives, 8 top tens, and 16 top twenties. Sadler led 21 laps in 2008, his fewest since the 2000 season. Sadler threatened a lawsuit for breach of contract; however, the lawsuit was dropped after the GEM – Petty Enterprises merger and he returned to the ride for 2009.
He ended the year 24th in the Sprint Cup Series standings. After all of the offseason issues Sadler found himself in the No.
He also had a wild flip at Michigan Speedway after cutting a tire in practice.
In 2001, Sadler won his first Cup victory at Bristol, making this the first win for Wood Brothers in eight years.
In 2007, Sadler led 62 laps, posted two top-10 finishes and finished 25th in points.
Sadler had the longest streak without a DNF than any other driver before failing to finish a race in 2007. 19 Best Buy Dodge for Gillett Evernham Motorsports in 2009.
He was recruited by over 20 universities to play college basketball, and ended up accepting a basketball scholarship from James Madison University in Harrisonburg, Virginia.
However, he injured his knee before his freshman season and needed two surgeries, eventually quitting school to focus on racing.Sadler began racing in go-karts at the age of seven, and moved up to the Late Model stock car division at the local race track.His accomplishments include over 200 total wins, the 1983–84 Virginia State Karting Championship, and the North Carolina Gold Cup in 1991–92.He also made sixteen starts for Robert Yates in the Busch Series, driving the No. In 2006, Sadler won the pole at Talladega and finished 22nd in points.He made seven starts in the Busch Series and his best finish was second at Richmond.When he turned 18, he moved to the Winston Racing Series and ran full-time beginning in 1993. In 1995, he was crowned track champion at South Boston Speedway, winning 13 races including a 6-race winning streak.