NASCAR Winston Cup 1999

1949 Red Byron • 1950 Bill Rexford • 1951 Herb Thomas • 1952 Tim Flock • 1953 Herb Thomas • 1954 Lee Petty • 1955 Tim Flock • 1956 Buck Baker • 1957 Buck Baker • 1958 Lee Petty • 1959 Lee Petty • 1960 Rex White
• 1961 Ned Jarrett • 1962 Joe Weatherly • 1963 Joe Weatherly • 1964 Richard Petty • 1965 Ned Jarrett • 1966 David Pearson • 1967 Richard Petty • 1968 David Pearson • 1969 David Pearson • 1970 Bobby Isaac • 1971 Richard Petty
• 1972 Richard Petty • 1973 Benny Parsons • 1974 Richard Petty • 1975 Richard Petty • 1976 Cale Yarborough • 1977 Cale Yarborough • 1978 Cale Yarborough • 1979 Richard Petty • 1980 Dale Earnhardt • 1981 Darrell Waltrip
• 1982 Darrell Waltrip • 1983 Bobby Allison • 1984 Terry Labonte • 1985 Darrell Waltrip • 1986 Dale Earnhardt • 1987 Dale Earnhardt • 1988 Bill Elliott • 1989 Rusty Wallace • 1990 Dale Earnhardt • 1991 Dale Earnhardt • 1992 Alan Kulwicki
• 1993 Dale Earnhardt • 1994 Dale Earnhardt • 1995 Jeff Gordon • 1996 Terry Labonte • 1997 Jeff Gordon • 1998 Jeff Gordon • 1999 • 2000 Bobby Labonte • 2001 Jeff Gordon • 2002 Tony Stewart • 2003 Matt Kenseth • 2004 Kurt Busch
• 2005 Tony Stewart • 2006 Jimmie Johnson • 2007 Jimmie Johnson • 2008 Jimmie Johnson • 2009