Ironically enough...3. He won the Daytona 500 in 1998 and the Pepsi 400 in 1990 and 1993.
While the above information is true in terms of points races in Sprint Cup, Dale Sr. actually won a total of 34 races at Daytona if you include Nationwide Series wins, Gatorade Duel Wins, Budweiser Shootouts, and IROC races.
If you count all events (not just the Daytona 500 and Pepsi 400), the #3 is the winningest number. Dale Earnhardt won 34 times in Cup, IROC, and Busch.
In the Winston Cup Series, Dale Sr. had 22 top 5 finishes in 46 starts at the Daytona International Speedway.
Dale Sr. started the Daytona 500 23 times from 1979 to 2001.
He has won the Daytona 500 2 times. Once in 2004 and once in 2014.
Dale Sr. finished second five times in the Daytona 500.1984, 1993, 1995, 1996, 1999.
"NEVER" He drives in Nascar, The INDY 500 is open wheel cars, (Champ & Indy) Never! Different type car.
Mark Martin competed in 236 Busch Series races, it is now known as the Nationwide Series.
Dale Earnhardt won the Gatorade Duels at Daytona a remarkable 5 times in a row from 1990 to 1994. This impressive streak showcases his dominance in these qualifying races during that era. His consistency and skill on the track made him a formidable competitor in the lead-up to the Daytona 500.
Richard Petty won the Daytona 500 seven times.1964, 1966, 1971, 1973, 1974, 1979, 1981
Kyle Busch won the most of his Sprint Cup Series races at Bristol Motor Speedway. He won five times there.
Jeff Gordon ran his first Busch Series race (now known as the Nationwide Series) on October 20, 1990. His first Cup Series race was on November 15, 1992. Jeff started to race full time in the Cup Series in 1993.
Through the 2011 season, Michael Waltrip has started 766Nascar Cup races, 279 Nationwide races (formerly known as the Busch Series) and 9 Truck Series races.