Trained by Martin L. Fallon, Jr., the colt raced head-to-head with four other outstanding horses: Harry Guggenheim's colt Bald Eagle, and future Hall of Fame inductees Round Table, Tim Tam, and Sword Dancer.
At age three, Hillsdale won five important races on both coasts, the last of which was the Malibu Stakes, the first leg of the Strub Series.
[3] He followed up by winning the San Fernando Stakes and the Santa Anita Maturity,[4] becoming the second of just five horses who have ever won the Strub Series.
[5] In thirteen starts in 1959, the four-year-old Hillsdale won ten important stakes, including seven in a row, and finished second in his other three.
In the Woodward Stakes at Aqueduct Racetrack, Hillsdale beat Round Table again but finished second to Sword Dancer.