After a 2-year-old season highlighted by seconds in two grade II races, Skip Away joined the Triple Crown trail in 1996. He won the Blue Grass Stakes and was second in the Preakness and Belmont after an uncharacteristic race in the Kentucky Derby. After the three Triple Crown races, he captured the Ohio Derby and Haskell. Later in the summer and fall, he won the Woodbine Million and then upset older champion Cigar in the Jockey Club Gold Cup, with Preakness winner Louis Quatorze running third. Skip Away was voted the champion 3-year-old.
At four, Skip Away lost early, but then won the Mass Cap and Suburban Handicap and climaxed his campaign with a second Jockey Club Gold Cup triumph and then a six-length defeat of Deputy Commander in the Breeders Cup Classic at Hollywood Park. He was voted the older male champion.
At five, Skip Away won his first seven races, all but two of them grade I events. He won the Donn at Gulfstream Park in Florida, the Pimlico Special in Maryland, and another Mass Cap (130 pounds). He then went West again to defeat Puerto Madero and Gentlemen in the Hollywood Gold Cup and completed his winning streak in the Iselin under 131 pounds back in New Jersey and the Woodward in New York before two dull races at the end of the campaign. He was voted champion older male again as well as Horse of the Year.