1999 NASCAR Winston Cup Series Rookie of the Year.

The first person to win Winston Cup Championship and The Nextel Cup Championship.

The only driver to complete the 1100-mile "Indy/Charlotte" double on Memorial Day Weekend. Stewart accomplished the feat in 2001, finishing sixth in the Indianapolis 500 before flying to North Carolina to race in the Coca-Cola 600, where he finished third. He also attempted the double in 1999 and was in the top ten in both races, but came up short of completing all the miles. Only John Andretti and Robby Gordon have also tried the feat, Andretti in 1994 (he crashed from the 600) and Gordon in 1997, 2000, 2002, 2003 and 2004, none ending with an 1100-mile workday.

Finished second to Dale Earnhardt Jr. in the 2004 Daytona 500.

In 2004, along with co-pilots Dale Earnhardt Jr. and Andy Wallace, drove the #2 CITGO Chevrolet Crawford Daytona Prototype to a fifth-place finish in the Rolex 24-Hour race at Daytona International Speedway.

2002 NASCAR Winston Cup Champion.

1997 Indy Racing League Champion.

In 2006, he donated $1 million to the Victory Junction Gang Camp.

2005 Winner of The Nextel Championship.

Winner of the 2005 Brickyard 400.