At age three Swain raced for the Godolphin Stables in France, where he won two conditions races (including the Grand Prix de Deauville), and was third to Lammtarra in record time in the 1995 Prix de l'Arc de Triomphe.
At four, he was second to Helissio in the 1996 Grand Prix de Saint-Cloud, won the Prix Foy, and defeated Singspiel to win the Coronation Cup in England. Shipped to North America for the 1996 Breeders' Cup Turf at Woodbine Racetrack, Swain finished third behind Pilsudski and Singspiel.
At age five in 1997, Swain defeated both Pilsudski and Helissio to win the 1997 King George VI and Queen Elizabeth Stakes. He returned in 1998 to repeat as the winner, making him (at age six) the oldest horse to win the King George VI and Queen Elizabeth Stakes and the first back-to-back winner since Dahlia in 1973–74. He also won the 1998 Irish Champion Stakes, but finished second in that year's Coronation Cup and second to Silver Charm in the Dubai World Cup. Sent to Churchill Downs in Louisville, Kentucky for the 1998 Breeders' Cup Classic, Swain wound up his racing career with a third-place finish to Awesome Again and Silver Charm.
After earning $3,797,566 in racing, Swain was retired to stud duty and currently stands at Shadwell Farm in Lexington, Kentucky.
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