At age three, under jockey George Seabo, Challedon finished second in the 1939 Kentucky Derby, eight lengths behind future Hall of Fame colt Johnstown.

[1] In 1940, the four-year-old Challedon continued his winning ways, claiming victory under jockey George Woolf in the Hollywood Gold Cup and the Whitney Stakes.

Beginning in September 1940, Don Cameron trained Challedon for owner William L. Brann and won the Pimlico Special and Havre de Grace Handicap.

The following year, for new trainer Edward Christmas Challedon returned to the winner's circle twice, including in the Philadelphia Handicap,[4] but had lost his drive and was retired to stand at stud at Gallaher Farm in Lexington, Kentucky.

While not a spectacular success as a sire, Challedon did produce thirteen stakes winners before passing away at the age of twenty-two after breaking a leg in his paddock.