Dale Earnhardt and his son Dale Jr donned similar hats at the 1990 Winston Cup championship ceremony. For the NASCAR fan who has disposable income laying around, this eBay item could be yours to own. A hat from Dale Earnhardt's incredible 1990 season, in which he won nine races en route to his fourth Winston Cup championship, is up for grabs on the auction site. A hat similar to what Dale Earnhardt was wearing after winning the 1990 Winston Cup. Earnhardt was seen holding the Winston Cup trophy at the end of the last race of the season in Atlanta, but it wasn't clear whether The Intimidator actually wore the listed item.