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In 1999, the legendary Wood Brothers, also native to Virginia, looked no further than their own backyard to find the driver for their No. 21 entry and signed Sadler to his first full-time NASCAR Cup Series ride. Their first victory together came in 2001 at Bristol Motor Speedway in Sadler's 75th career start. The win in "Thunder Valley" was monumental for two reasons. First, Sadler started deep in the field in the 38th spot. More importantly, it returned the Wood Brothers to victory lane for the first time since 1993.
After four seasons, Sadler and the Wood Brothers parted ways and the Virginia native headed for Robert Yates Racing (RYR). Sadler had two Bud Poles (Darlington Raceway and Talladega Superspeedway) in 2003 with his No. 38 team. He completed the year with two top-five and nine top-10 finishes which earned him a 22nd-place finish in the season point standings. Energy was infused into Sadler's team with personnel changes during the off-season, setting the stage for Sadler's most successful season to date.
His 2004 season proved to be a breakout one as the Virginia native surprised many in the garage area. Sadler struck early at the season opening event as Daytona International Speedway by winning the outside pole for the Daytona 500. Later in Speedweek, he won in the Gatorade Twin 125 qualifying event that gave primary sponsor M&M's their first ever trip to Victory Lane.
Success was sweet and continued throughout the season as Sadler saw more of the same with an emotional win at Texas Motor Speedway. Later in the season Sadler scored his third career victory at California Speedway, clinching a position in the inaugural NASCAR Sprint Cup Chase for the Championship. Sadler was one of four drivers to stay in the top 10 in the point standings the entire season and rounded out the year with two wins, eight top-five and 14 top-10 finishes. He finished ninth in the final standings.
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