Bred by Anna Marie Barnhart, Skip Away was foaled and reared at Hilmer Schmidt's Indian Hill Farm in Florida.
He won the 1996 Haskell Invitational Handicap and in October of that year, he defeated Cigar, winner of 17 of his previous 18 races, in the Jockey Club Gold Cup at Belmont Park.
With Bailey at the reins, Skip Away adopted a new front-running style and won nine consecutive races, including a six-length victory in the 1997 Breeders' Cup Classic, contested that year at Hollywood Park Racetrack, setting a record time of 1:59:16 under another new rider, Mike Smith.
As a five-year-old, Skip Away won seven consecutive races including five Grade I events, such as the 1998 Pimlico Special, Hollywood Gold Cup, and Woodward Stakes.
[3] At age seventeen, Skip Away died of an apparent heart attack in his paddock on May 14, 2010 at Hopewell Farm in Midway, Kentucky.