His background is in open-wheel racing, and he won races in IndyCars for Derrick Walker, also running his own team in the late 1990s. He has also competed in the Indy Racing League. In 1999, Gordon came within two laps of winning the Indianapolis 500. He inherited the lead by virtue of not stopping for a final pit stop and the tried to conserve enough fuel to last until the end of the race. He ran out on lap 199 (of 200) and had to give up the lead to Sweden's Kenny Brack. In 2002, Helio Castroneves tried almost exactly the same move and won when a crash brought out the caution flag at the end of the race and allowed him to coast the last two laps.

For 2005, Gordon is running his own team in Nextel Cup. He is the only owner/driver currently in Nextel Cup. Robby’s primary sponsor is Jim Beam Whiskey, his crew chief is Greg Erwin. Fruit of the Loom will have the temporary privilege of playing primary sponsor for 9 races in the 2005 season. Menards will also be the primary sponsor in some select races, as will Harrah's.

Robby is a six-time off-road racing champion, and has also raced in the NASCAR Busch and Craftsman Truck series, Trans-Am, GTO, Champ Car, where he scored two wins, and the Indy Racing League. In 2005 Gordon took part in the famous 16 day Dakar Rally, driving for the Red Bull sponsored Volkswagen team. He became the first American in the history of the rally to win a stage in the car division. He won two stages in total and a 12th place division finish. Gordon also won the 2005 Baja 500 covering the 419-mile course in 9 hours, 10 minutes, 32 seconds.

In the 2005 Sylvania 300, he was involved in a wreck with driver Michael Waltrip the driver of the #15 NAPA Chevorlet. The angered Gordon got out of his totaled car and threw his helmet at the #15 car as it was passing by, nearly getting run over by Chase to the cup contender Tony Stewart. When TNT interviewed him about the crash he stated "People think he's a nice guy, but he's not, he's just a piece of shit." TNT apologized for his language, and Gordon apologized after the race, but Gordon was fined $50,000 USD and docked 50 drivers points. When asked by some poeple for the helmet, Gordon decided to auction it for the benefit of the Harrah's Employee Relief Fund, a fund that provides aid to Harrah's employees displaced by Hurricane Katrina. The helmet fetched $51,100.