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. 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 (
Brantôme, probably the best three-year-old of 1934 was a sick horse during the summer) 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." Windsor Lad prevailed in the race, beating Easton by a length and a half. He won the Rous Memorial Stakes over 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. ==Assessment==