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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.

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