He was described as "a good, hard bay, level of back, with a well-placed shoulder and broad hips" who possessed a "resolute and calm" temperament.

[2] Windsor Lad was sent into training with Marcus Marsh at Newmarket, Suffolk and accompanied his trainer when he relocated to Lambourn after the 1933 season.

Windsor Lad was ridden in most of his races by Charles "Charlie" Smirke, a controversial figure who was returning after being "warned off" (banned) for five years after he was suspected of "stopping" a horse.

[3] Windsor Lad won two races as a juvenile including the Criterion Stakes at Newmarket in October,[4] but was slow to mature and was not among the leaders of his generation.

In 1934, Windsor Lad emerged as a Derby candidate by winning two trial races, the Chester Vase on 8 May[5] and the Newmarket Stakes.

The Maharaja celebrated with a lavish party at the Savoy Hotel which featured a performing elephant arrayed in his purple and cream racing colours.

[11] In front of a crowd estimated at a quarter of a million,[12] Smirke tracked the leader before moving the colt in to the lead three furlongs from the finish.