Kentucky Derby and Later Career
Old Rosebud came back in his third year to take the 1914 Kentucky Derby by eight lengths in a time of 2:03 2/5, setting a record that would not be broken for 16 years. In the Derby, he had begun the race as the favorite because of his previous record.
Three weeks after the Derby, Old Rosebud sustained a bowed tendon during the May 1914 running of the Withers Stakes at Belmont Park. The race was run clockwise around the track instead of the more customary, in the U.S., counter-clockwise direction. Running the wrong way confused Old Rosebud, who did not change leads coming into the stretch. He was taken out of competition for two seasons as a result of the injury.
At age 6, after nearly three years on the prairies of Texas, Old Rosebud won the Queen's County, the Carter Handicap, the Red Cross, and the Delaware Handicap. These victories also led to his being named historical Champion Handicap Male of 1917. An injury took him out of competition for another year and a half.
Old Rosebud returned to racing at the age of 8. Overall, he won the Yucatán Stakes, the Spring Trial Stakes, the Harold Stakes, the Cincinnati Trophy Stakes, the Flash Stakes, the United States Hotel Stakes, and the Kentucky Derby.
He went on to win the Clark Handicap, the Latonia Inaugural Handicap, the Queens County Handicap, the Carter Handicap (again), the Frontier Handicap, the Delaware Handicap, the Bayview Handicap, the Mt. Vernon Cap, the Sir Archy Highweight Cap, and the Latonia Grand Hotel Purse. He came in second in the Idle Hour Stakes, the Bashford Manor Stakes, the Paumonok Handicap, the Mount Vernon Handicap (losing to the four-years-younger August Belmont, Jr.'s Lucullite, but beating Sun Briar, Exterminator's stablemate), and the Burnett Woods Cap (to the five-years-younger stakes-winning Sennings Park). He was third in the Brooklyn Handicap, the Thanksgiving Handicap, and the Eden Park Cap.
Old Rosebud competed for a total of 10 years before suffering his final injury in a claiming race at Jamaica Racetrack. He had to be euthanized. Out of 80 starts, Old Rosebud won 40, placed in 13, and showed in 8. His career earnings were $74,729.
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