At age two Hill Prince won six of the first seven races he entered, his only defeat coming when he failed to recover from a poor start in the Sapling Stakes.
From the start of the 1950 season, Hill Prince was regarded as one of the main contenders for the Triple Crown races, along with Oil Capitol, Middleground, and the Californian colt Your Host.
[7] Less than a week after this effort, Hill Prince re-established his position at the head of the Derby contenders with a two-length win over a strong field, including Middleground, in the Wood Memorial.
In August, Hill Prince faced a field including Your Host in the American Derby and displayed "blistering speed" in the last six furlongs to win by one and a half lengths from All Blue.
[14] In the Jockey Club Gold Cup over two miles at Belmont in October, Hill Prince established his position as the best horse in America as he "cakewalked" to a four length victory over the Irish-bred Noor.
[15] In November, Hill Prince was sent to California to take on Your Host on the latter's home ground in the Thanksgiving Day Handicap and was beaten in a photo finish in front of "40,000 howling fans".
[16] Hill Prince stayed in California for his last two starts of the year: he finished third to Noor in the Hollywood Gold Cup and then won the Sunset Handicap, coming from the back of the field to overtake the champion filly Next Move in the closing stages.
[18] In January 1951, Hill Prince sustained a broken bone in his right hind leg when being prepared for the Santa Anita Maturity[19] and was forced to miss the first eight months of the season.
[20] In the following month Hill Prince failed to repeat his win in the Jockey Club Gold Cup when he was caught close to the finish and narrowly beaten by Counterpoint.