In 2003, Matt Kenseth won the last Nascar Winston Cup Series championship. The following season the series was known as the Nextel Cup. The name was again changed in 2008 to the Sprint Cup.
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NASCAR's top tier series, the Winston Cup Series, changed its name after the 2003 season, due to sponsor R.J. Reynolds leaving the series due to pressure from lobbyist to remove tobacco advertising from sports. Therefore, in 2004, the series became the "Nextel Cup Series" (later changed to "Sprint Cup" due to the merger between Nextel and Sprint)
Therefore, the last winner of the "Winston Cup" was Matt Kenseth.
The Top Ten for the 2003 Season
In 1971, Richard Petty won the first Nascar championship award named the "Winston Cup". Prior to this, the series was known as the Strictly Stock Series (1949) and then the Grand National Series (1950-1970).
Matt Kenseth won the last title known as the Winston Cup Series championship, in 2003.
In 2012, Brad Keselowski became the latest driver to win the Nascar Sprint Cup Series championship.