In May, Gallant Fox started as the favorite for the Preakness Stakes, that year the first of the "Triple Crown" races. Ridden by Earl Sande, he took the lead early in the straight and held the late challenge of Crack Brigade by three quarters of a length. The win was enthusiastically received with the popular Sande smiling and raising his whip to the crowd. The Kentucky Derby, two weeks later, attracted a crowd of 50,000 despite heavy rain at Louisville, and Gallant Fox started favorite. He broke slowly but took the lead on the backstretch from the filly Alcibiades before winning by two lengths from Gallant Knight, completing the course in 2:07 3/5 on a muddy track. Sande won the race for a record third time, following victories on Zev and Flying Ebony. By this time, Gallant Fox was becoming known as "the red-headed-horse" because of the bright red hood he wore in his races. At Belmont Park three weeks later, he won the Belmont Stakes from Whichone, who had missed the Derby but won the Withers Stakes and had been favored to win by many "experts". Before the end of June, Gallant Fox added a win in the Dwyer Stakes at odds of 1/10, although the lack of effective opposition (Whichone missed the race through injury) made the victory a "hollow" one. By July, Gallant Fox was being described as a "super horse" and about 60,000 were in attendance at Arlington Park near Chicago when he won the Arlington Classic by a neck from Gallant Knight with the top weight of 126 pounds.