[8] Ridden by the Australian jockey Frank Bullock he became unbalanced on the downhill section of the course before producing some "devouring strides"[8] to take the lead in the closing stages and won by one and a half lengths from Solario, with Manna a neck away in third place.
[10] Picaroon began his second season as a leading fancy for The Derby, with his pedigree suggesting that he would be capable of staying the one and a half mile distance.
[6] On his three-year-old debut he started favourite for the Craven Stakes at Newmarket in April and won easily from his stablemate Cross Bow[11] with Solario in third.
Although he looked impressive before and during the race it was noted that the conformation of his legs was faulty: he had "rough" hocks and inward-turning "toes" which were thought likely to put undue strain on his tendons.
[17] Picaroon returned to form at Newbury Racecourse later in September when he started 4/11 favourite for the Kingsclere Plate and won easily by two lengths from the King's colt Runnymede.
At Newmarket in October Picaroon again started odds-on favourite when facing four opponents, and produced what was described as a "whirlwind" finish to beat Rufus O'Malley by two lengths.
[18] Two weeks later he was matched against the five-year-old Pharos in a two-runner race for the Champion Stakes over ten furlongs at Newmarket and won by half a length from his older rival.
[20] In the Free Handicap, an official ranking of the best two-year-olds to race in Britain, Picaroon was the top-rated colt of 1924, one pound behind the filly Saucy Sue, who was also trained by Taylor.