Pastrana has won two motocross racing championships: the 2000 A.M.A. 125cc National championship, and the 2001 125cc East Coast Supercross Championship. Pastrana also raced in the 2000 MX des Nations. He moved up to the 250cc class in 2002. His stand-up style, ability to spot jump combinations and great speed through the whoops make him easy to spot on the track. Although Pastrana has never won a 250cc race, his kindness to the fans and love of the sport still makes him one of the most popular riders of all time. Pastrana has always raced and competed on Suzuki motorcycles, and remains fiercely loyal to the brand. He races with Team Cernic's Suzuki. All of his motorcycles and rally cars carry the number 199. He even sponsors a Monster Jam truck called Pastrana 199, and Nitro Circus after the TV show on MTV.
In 2003, Pastrana opened a rallying career in the Race of Champions, and began driving for the Subaru-backed Vermont SportsCar rally team in 2004. Starting in 2006, Pastrana was signed by Subaru to lead their new Subaru Rally Team USA, being paired once again with veteran co-driver Christian Edstrom. On August 5, 2006 Pastrana won the gold medal in the first rally car competition at the X Games, edging out rally legend Colin McRae by 0.53 seconds after McRae rolled his car through the last jump.
Pastrana and Edstrom clinched the 2006 Rally America National Series overall and open class championship on October 22, 2006 during day one of the Lake Superior Performance Rally. The team finished out the 2006 series with another first-place victory at the Wild West Rally in Olympia, Washington on December 31, 2006.
On December 16, 2006 Pastrana competed at the 2006 Race of Champions at the Stade de France in Paris. He represented the United States in the Nations' Cup by himself, after injuries forced teammate Jimmie Johnson and his replacement Scott Speed to withdraw.
February 19, 2007 brought news that Pastrana's longtime co-driver Edstrom had announced a sabbatical to concentrate on his career and family. Although former McRae co-driver Derek Ringer is set to compete with Pastrana for the 100 Acre Wood Rally in Salem, Missouri and Rally America, he has not announced a permanent replacement co-driver.
Pastrana driving a classic Ford Escort Mk1 at the 2008 Colin McRae Forest Stages.
In September 2008, Pastrana took part in the Colin McRae Forest Stages Rally, a round of the Scottish Rally Championship centred in Perth in Scotland. Derek Ringer was his co-driver and they entered in a historic Ford Escort RS1600. He was one of a number of celebrity drivers to take part in the event in memory of McRae, who died in 2007.
On August 29, 2009 Pastrana claimed the overall victory at Ojibwe Forests Rally, his fifth of the 2009 Rally America season. The victory sealed his fourth consecutive Rally America driver's title, the most in series history.
