The past winners of the Gold Cup are a veritable who's who of award-winning Hall of Fame horses, including Easy Goer, Man o' War, Cigar, Skip Away, Curlin, Slew o' Gold, John Henry, Affirmed, Forego, Shuvee, Damascus, Buckpasser, Kelso, Sword Dancer, Nashua, Citation, Whirlaway and War Admiral.
Despite the current $1,250,000 purse and Grade 1 status, the stature of the race has suffered somewhat in recent years thanks to the emergence of the Breeders' Cup Classic held not long afterward, as well as a change in distance to 1+1⁄4 miles in 1990, reducing its distinctiveness.
Damask, owned by Harry Payne Whitney, was entered as a sporting gesture and to keep Man o' War from having to run alone in a "walkover."
Damask finished 15 lengths behind with Man o' War held under strong restraint in order not to humiliate his rival.
In 2021 the Jockey Club Gold Cup was moved to Saratoga Race Course for the first time in its history.