Street joined the U.S. Ski Team in 1989 at the age of 17. She primarily competed in the speed events of downhill and super G, with her World Cup debut at age 21 in a slalom on December 6, 1992. Two months later at the 1993 World Championships in Japan she won the silver medal in the combined event.
After her silver medal performance in the downhill at the 1994 Winter Olympics, a run was named after her at Sun Valley, on the Warm Springs side of Bald Mountain; the expert run formerly known as "Plaza" became "Picabo's Street."
By winning the 1995 downhill title, she became the first American to win a World Cup season title in a speed event. She repeated as downhill champion the following season, adding the title of world champion with her gold medal at the 1996 World Championships in Sierra Nevada, Spain.
In early December 1996, she suffered a knee injury training in Colorado after competing in just two races, and sat out the remainder of the 1997 season. A month after her gold medal win in the super G at the 1998 Winter Olympics, Street careened off course while racing at the final downhill of the 1998 season at Crans-Montana, Switzerland. She crashed, snapping her left femur and tearing a ligament in her right knee. She was in rehabilitation for two years following the accident.
Street returned to ski racing in late 2000, and retired from international competition after the 2002 Winter Olympics in Utah, where she finished 16th in the downhill.