1990 NASCAR Winston Cup SeriesPrevious1989Next1991 The 1990 NASCAR Winston Cup Series was the 42nd season of professional stock car racing in the United States and the 19th modern-era Cup Series. It began on Sunday, February 11, and ended on Sunday, November 18. Because of a highly controversial penalty to Mark Martin early in the season, Dale Earnhardt with Richard Childress Racing was crowned the Winston Cup champion for the fourth time, edging out Martin by 26 points.