In the Newmarket Classic on 27 April he started 6/1 third favourite and finished fifth behind Disraeli. He was moved up to ten furlongs for his next start, but finished fifth again in the Newmarket Stakes on 11 May behind the easy winner Cyllene, a colt who had not been entered in the classics. Jeddah was "in trouble all the way" and looked a most unlikely Derby contender. Jeddah was given little chance in the Derby at Epsom on 25 May, and started at 100/1 in a field of eighteen. He was ridden in the race, his first outside Newmarket, by Herbert "Otto" Madden, who was in the process of winning his first Championship. Jeddah was held up towards the rear of the field in the early stages as the 2/1 favourite, Disraeli made the running. Disraeli weakened soon after half way and Batt led the field into the straight. Madden moved Jeddah steadily forward into third place before making his challenge two furlongs out. He overtook the Batt inside the final furlong and won by three quarters of a length after a "game struggle", with another 100/1 outsider, Dunlop, finishing third. The win for the "free-striding giant" was greeted in "solemn silence" by the "dumbfounded" crowd. At Royal Ascot, Jeddah, ridden by John Watts, improved on his Derby-winning performance in the Prince of Wales's Stakes by giving six pounds to Batt and beating him "without an effort" by five lengths. Jeddah was then trained for the St Leger at Doncaster but his preparation was seriously disrupted by an injury to a suspensory ligament. No official announcement of the injury was made, but Jeddah's performance in a public exercise was unimpressive and his odds drifted out from 2/5 two days before the race to 5/6 at the start. Jeddah tracked the leaders before Watts sent him into a clear lead early in the straight, but he was caught a furlong from the finish and beaten four lengths by Wildfowler. It was suggested after the race that Jeddah had been unable to extend himself on the hard ground. Jeddah stayed in training at four, but became increasingly difficult to train, with his left foreleg causing particular problems. He was not seen on a racecourse until September 28, when he ran in the Jockey Club Stakes at Newmarket.