The 1999 Daytona 500, the 41st running of the event, was held February 14, 1999, at Daytona International Speedway. Jeff Gordon won the pole and won the race, making him the first Daytona 500 pole sitter to win the race since Bill Elliott in 1987

This race was known for Jeff Gordon's daring three-wide pass on Rusty Wallace and Mike Skinner. He passed Wallace after ducking to the apron, nearly plowing into the damaged car of Ricky Rudd. Skinner jumped to the outside and they raced three-wide for three laps until Dale Earnhardt (the defending Daytona 500 winner) gave Gordon the needed push. The race was also known for a determined Earnhardt repeatedly trying to pass Gordon for the lead on the final lap, only for Gordon to beat him to the finish. The race had a 13-car pileup on lap 135, in which eventual series champion Dale Jarrett flipped over twice but however, he was uninjured.