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Gen. Duke raced twice as a two-year-old, with a single maiden win and a third. As a three-year-old, he faced eventual 3-year-old champion Bold Ruler 4 times leading up to the Kentucky Derby, with each winning twice. At Hialeah Park, Gen. Duke ran second to Bold Ruler January 30 in the mile Bahamas Stakes, with Bold Ruler giving up 12 pounds. Gen. Duke, again receiving 12 pounds from his rival, won the mile Everglades Stakes February 15. At equal weights, Gen. Duke finished second by a neck to Bold Ruler on March 2 in the mile Flamingo Stakes, with the winner establishing a new track record of 1:47. In their fourth and final meeting March 30 in the mile Florida Derby at Gulfstream Park, Gen. Duke, with Hall of Fame jockey Bill Hartack aboard and coupled with eventual Kentucky Derby winner Iron Liege in the 5 horse field, defeated Bold Ruler at equal weight of 122 pounds by lengths in the final time of 1:. His winning time established a new track record, equaled the world record held by Noor, Alidon, and Swaps, and continues to be the fastest Florida Derby ever run.