Posting a modern NASCAR series record of 22 top five finishes in 1983 and 21 top five finishes both in 1981 and 1986, Waltrip won 84 NASCAR Cup Series races, including the 1989 Daytona 500, a record five in the Coca-Cola 600 (formerly the World 600) (1978, 1979, 1985, 1988, 1989), and a track and Series record for any driver at Bristol Motor Speedway with 12 (seven consecutive from 1981 to 1984). Those victories tie him with Bobby Allison for fourth on the NASCAR's all-time wins list in the Cup Series and place him second to Jeff Gordon for the most wins in NASCAR's modern era. He is ranked fifth for all-time pole positions with 59, including all-time modern era highs with 35 on short tracks and eight on road courses. Competing in 809 Cup starts over four decades and 29 years (1972–2000), he has scored 271 Top 5s and 390 Top 10s. Winning nearly $19.9 million in posted earnings, he became the first NASCAR driver to be awarded over $10 million in race winnings.
Waltrip has additionally won 13 NASCAR Busch Grand National Series races, seven American Speed Association (ASA) races, three IROC races, two Automobile Racing Club of America (ARCA) races, two NASCAR All-American Challenge Series events, two All Pro Racing Association races, and a USAC race. He competed in the 24 Hours of Daytona. He also holds the all-time track record 67 wins at the Fairgrounds Speedway in Nashville, Tennessee, including NASCAR, USAC, ASA, and local Late Model Sportsman NASCAR sanctioned series races. He still holds many NASCAR records, more than two decades after his retirement as an active driver.
He has also won many awards in NASCAR. That includes two for NASCAR's Most Popular Driver Award (1989, 1990), three for "American Driver of the Year" (1979, 1981, 1982), and "NASCAR's Driver of the Decade" for the 1980s, as well as three for "National Motorsports Press Association Driver of the Year" (1977, 1981, and 1982), two for "Auto Racing Digest Driver of the Year" (1981 and 1982), the first "Tennessee Professional Athlete of the Year" (1979), one of NASCAR's 50 Greatest Drivers in 1998, and the Bill France "Award of Excellence" in 2000. He has been inducted into numerous halls of fame, including the Motorsports Hall of Fame of America for 2003 the International Motorsports Hall of Fame for 2005. After being nominated for the inaugural 2010 and 2011 classes, he was inducted into the NASCAR Hall of Fame's 2012 class.

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