Windsor Lad was sired by the three-time Champion sireBlandford out of the 1926 Epsom Oaks runner-up Resplendent. 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. As a yearling he was sent to the sales by his Irish breeder, Dan Sullivan, where he was sold for 1,300gns to the Indian Maharaja of Rajpipla. 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" for five years after he was suspected of "stopping" a horse.
Racing career
1933: two-year-old season
Windsor Lad won two races as a juvenile including the Criterion Stakes at Newmarket in October, but was slow to mature and was not among the leaders of his generation.
1934: three-year-old season
In 1934, Windsor Lad emerged as a Derby candidate by winning two trial races, the Chester Vase on 8 May and the Newmarket Stakes. In The Derby he started at 15/2 joint second favourite, in a field of nineteen, with the undefeated 2000 Guineas winner Colombo starting favourite. The race was run of fast ground in front of a crowd estimated at between 300,000 and 500,000. Ridden by Charlie Smirke, Windsor Lad was second turning into the straight before taking the lead a furlong out. He was strongly challenged by Easton and Colombo but ran on strongly to win by a length and a neck. The winning time of 2:34.0 equalled the race record set by Hyperion the previous year. The Maharaja celebrated with a lavish party at the Savoy Hotel which featured a performing elephant arrayed in his purple and cream racing colours. Windsor Lad started favourite for his first race against older horses in the Eclipse Stakes at Sandown in July. Smirke held the colt up but became "jammed against the rail" in the straight. By the time he had extricated the Derby winner, the race was effectively over and although Windsor Lad finished strongly he finished only third, beaten half a length and the same by the four-year-olds King Salmon and Umidwar. During the summer of 1934 there were proposals for special international race at either Saratoga Springs or Belmont Park between Windsor Lad, the American champion Cavalcade and the leading French colt Admiral Drake but the plans did not come to fruition. After the Eclipse Stakes, Windsor Lad was sold for a sum of £50,000 to the bookmaker Martin H. Benson. Windsor Lad won the Great Yorkshire Stakes and in the St Leger at Doncaster the colt returned to his best form. He started at odds of 4/9 with the connections of his rivals conceding that they had little prospect of upsetting the favourite. In front of a crowd estimated at a quarter of a million, Smirke tracked the leader before moving the colt in to the lead three furlongs from the finish. Windsor Lad was never challenged and won going away by two lengths from Tiberius in a record-equalling time of 3:01.6. As of 2012, the record remains unsurpassed. After the race he was described as "one of the finest horses the English turf has seen in many seasons."
1935: four-year-old season
Windsor Lad was unbeaten as a four-year-old. After winning the Burwell Stakes he faced Easton in the Coronation Cup at Epsom. The race was much anticipated, and was seen as being a match between Easton's speed and Windsor Lad's stamina. Windsor Lad prevailed in the race, beating Easton by a length and a half. He won the Rous Memorial Stakes over seven and a half furlongs at Royal Ascot and was then sent to Sandown for a second attempt at the Eclipse Stakes. In the Eclipse he started at odds of 4/7 and led from the start to win by three quarters of a length from Theft and Fair Trial. He broke down during the race and won what had already been announced as his last racecourse appearance despite sustaining an injury.
Windsor Lad suffered from ill health during his stud career and made little impact as a stallion. He developed severe sinus trouble and was put down on 14 December 1943. His most notable offspring was the Irish Triple Crown winner Windsor Slipper.