The top 5 all-time winningest drivers in the Nascar Cup Series are:
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Ralph Dale Earnhardt, Sr. Earnhardt is notable for his success in the Winston Cup Series, winning seventy-six races. Earnhardt's seven championships are tied for most all-time with Richard Petty.
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Richard Petty: 200 wins.
7 championships.
Most Poles (123).
Most wins in a season (27 in 1967).
Most wins in a row (10 in 1967).
Won Daytona 500 7 times.
NASCAR Hall of Fame in 2010.
International Motorsports Hall of Fame in 1997.
Motorsports Hall of Fame in 1989.
I believe that David Pearson(1970-80's) and Earnhardt Sr. both have 10 wins there.
All time is Richard Petty with 200.
Through 9/6/2011, Jeff Gordon leads active drivers with 85 wins.
David Pearson won ten Nascar Cup Series races at Darlington Raceway, the most by any driver. Dale Earnhardt Sr. is second with nine wins.