Harry Gant
Neil Bonnett
Darrell Waltrip
In 2003, Bobby Labonte was the last Winston Cup race winner and Matt Kenseth won the Winston Cup championship.
Jeff Gordon was the 2001 Winston Cup champion.
Kevin Harvick was 25 years old, when he won his first Winston Cup race at Atlanta in 2001.
Dave Dion's first Winston Cup race was in the #28 car. He drove the #29 in ten races and the #95 in one race.
In the NASCAR Sprinr Cup Series, the oldest driver is Mark Martin. He is ranked 13, 305 points behind at the time of this question. Mark is 50 years old.
There has never been a driver to win both the Busch (now the Nationwide Series) and the Winston Cup (now the Sprint Cup Series).
It is no longer known as the Winston Cup, it is known as the Sprint Cup Series now and the winner of the 2008 championship is Jimmie Johnson, Driver of the 48 Lowes Chevrolet for Hendrick Motorsports.
Eddie Hill would be my best guess (retired 1999 at age 63) Peston Welsh who's 84 as of 2009. Per Wikipedia: Paul Newman, at the age of 70 years and 8 days, became the oldest driver to be part of a winning team in a major sanctioned race,
In 2003, Matt Kenseth won the last Winston Cup Series championship. The following season it was renamed the Nextel Cup Series.
In 2003, Matt Kenseth won the last Winston Cup Series championship. The following season it was renamed the Nextel Cup Series.