Skywalker was trained by Michael Whittingham and raced under the Oak Cliff Stable partnership led by Thomas Tatham. He began racing in California in 1984 at age two where he won one of his two starts and was off the board in the other. In his three-year-old campaign, Skywalker made five starts, winning twice. His most important victory came under future U.S. Racing hall of Fame jockey, Laffit Pincay, Jr. when they won the most important West Coast race for three-year-olds, the Santa Anita Derby. He was then sent to Churchill Downs for the Kentucky Derby where jockey Eddie Delahoussaye rode him to a sixth-place finish behind winner, Spend A Buck.
In 1986, the four-year-old Skywalker had his best year in racing. That year he won the Longacres Mile, the Mervyn Leroy Handicap, and the San Diego Handicap then topped off the year with a win on the familiar ground of California's Santa Anita Park in the Breeders' Cup Classic. Ridden by Laffit Pincay, Jr., Skywalker defeated the heavy favorites Turkoman and Precisionist, who finished second and third respectively, as well as the European star Triptych who finished sixth.
Sent back to race at age five, Skywalker's best result in 1987 was a second place finish in the Arcadia Handicap and a third in the Goodwood Handicap. Retired to stud duty at Cardiff Stud Farm in Creston, California, he notably sired Bertrando, the 1993 Eclipse Award winner for American Champion Older Male Horse. Skywaker was also the damsire of Sky Jack, a Hollywood Gold Cup winner.
Moved to his birthplace at Stone Farm in 1996, Skywalker died of a heart attack at age twenty-one on February 25, 2003. He is buried in the Stone Farm equine cemetery.