Skip Away, a gray thoroughbred race horse, was named America's Champion 3 Year Old Male in 1996 and twice (1997, 1998) named America's Champion Handicap Horse. Foaled in Florida, the son of Skip Trial, out of the Diplomat's Way mare Ingot Way, was purchased for the modest sum of $22,500 as a yearling by Hall of Fame trainer Hubert "Sonny" Hine for his wife Carolyn, who had particularly wanted a gray horse because vision problems made it difficult for her to see any other kind on the race track.
Skip Away won but once from six starts as a two-year-old, placing in both the Cowdin and Remsen Stakes at Belmont Park. His first Stakes win came as a three-year-old, when he defeated eventual Preakness Stakes winner Louis Quatorze by six lengths in the Blue Grass Stakes while setting a new stakes record over a wet-fast track at Keeneland Race Course.
After an unaccountably poor performance in the Kentucky Derby, he finished second in both the Preakness and Belmont Stakes, losing the latter by a length to Editor's Note after a prolonged duel over the long Belmont stretch. He won the 1996 Haskell Invitational Handicap and in October of that same year, he defeated the mighty Cigar, winner of 17 of his previous 18 races, in the Jockey Club Gold Cup at Belmont Park. Seizing the lead entering the stretch, Skip Away held clear to win a stretch drive by a head over the steadily closing champion.
Formal Gold defeated Skip Away in 4 of their 6 meetings in 1997. After Skip Away was soundly defeated as a four-year-old by Formal Gold in the Philip H. Iselin Breeders' Cup Handicap at Monmouth Park and the Woodward Stakes at Belmont Park, he was given a new rider, Jerry Bailey, who replaced Shane Sellers. With Bailey at the reins, Skip Away adopted a new front-running style; and he proceeded to win 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 he won five Grade I races, including the 1998 Pimlico Special, Hollywood Gold Cup, and Woodward Stakes; and although he failed to repeat his Breeders' Cup win at Churchill Downs, he was nonetheless voted the Eclipse Award as both Champion Handicap Horse and Horse of the Year for 1998. He was retired to stud that fall with 18 wins and 34 in-the-money finishes from 38 career starts, his career earnings having amounted to $9,616,360.
Skip Away was inducted into National Museum of Racing and Hall of Fame in 2004. In the Blood-Horse magazine ranking of the top 100 U.S. thoroughbred champions of the 20th Century, Skip Away was ranked No.32.
In 2001, Gulfstream Park Racetrack in Hallandale Beach, Florida honored Skip Away by renaming its Broward Handicap the Skip Away Handicap.
At age seventeen, Skip Away died of an apparent heart attack in his paddack on May 14, 2010 at Hopewell Farm in Midway, Kentucky.