1999 - Pastrana wins the first ever MotoX Freestyle event at the X-Games. He also scored the highest ever run of 99.00 points.
2000 - Pastrana wins the gold medal first time
2001 - Pastrana wins his third gold, still the only person to win the event.
2003 - Pastrana reclaims his gold and becomes the second rider ever to complete a 360 in competition.
2004 - Pastrana crashed trying a 50ft 360, sustaining a concussion, but was able to compete the next day and won a silver medal. Nate Adams became the only rider to beat Pastrana at that time. Before this event, he had won Bronze in Best Trick, performing a One-Handed 360 and a Superman Seat Grab-Indian Air Back flip.
2005 - Pastrana won his fifth gold in Freestyle and also attempted the first ever Back flip Barspin on a motorcycle, however the bike failed and he resorted to a regular bike and performed a Back flip Saran Wrap to take Silver in Best Trick.
2006 - Pastrana became the third athlete to win 3 Gold medals at one X Games Event. He won Gold in MotoX Best Trick and Freestyle and Rally Car. Pastrana also performed the first Double Back flip in competition, scoring a 98.60, the highest score in the Best Trick competition at X Games.
2007 - Pastrana took bronze in Rally after sliding into the other drivers area while inside the Home Depot Center. He was disqualified but retained his medal. He also competed in the first MotoX Racing at X Games, but didn't achieve a medal after 2 false starts in the heat race and last chance qualifier.
2008 - Pastrana takes gold in Rally and competed in the Speed and Style event but didn't place.
2009 - Pastrana attempts a rodeo 720 at X Games 15 in the Moto X Best Trick Event. He crashed on his first attempt and withdrew from his second after having blurred vision. He placed 4th for his efforts. He took silver in Rally after being defeated by rookie and former Indy Car/Indy 500 champion Kenny Bräck.