Sir Hugo began his three-year-old season on 4 May by running in the 2000 Guineas, a race which was considered very open after the withdrawal of the favourite Orme.
He raced prominently, showing in third place at one stage, before finishing sixth of the fourteen runners behind Bona Vista
In the Derby on 1 June at Epsom Sir Hugo started at odds of 40/1 in a field of thirteen with La Fleche, who had won the 1000 Guineas being made the 11/10 favourite.
He was ridden by the lightweight jockey Fred Allsopp, who had to carry more than 28 pounds of "dead weight" to make the stipulated 126 pounds.
The weather was "gloriously fine" and the crowd was larger than usual.
After several false starts which delayed the race by half an hour, the early running was made by Thessalian and Persistive with Sir Hugo just behind the leaders.
The French-trained colt Bucentaur took the lead turning into the straight.
Sir Hugo moved past Bucentaur a furlong from the finish and was strongly challenged by La Fleche.
Cheered on by the bookmakers, Sir Hugo prevailed by three quarters of a length from the filly after a "desperate struggle", with Bucentaur a length further back in third Lord Bradford received £7,000 in prize money, but far more in winning bets, having backed Sir Hugo for the race at 100/1 before he ever ran.
There were many observers who considered Sir Hugo's win to have been a "fluke".
George Barrett, the rider of La Fleche, was criticised for giving the filly too much ground to make up while others drew attention to a collision between St. Angelo and Rueil at Tattenham corner which ended both colts' chances.

Sir Hugo was then sent to Royal Ascot where he started 4/6 favourite for the St. James's Palace Stakes over one mile.
He led into the straight but was overtaken in the last quarter mile and finished third behind St Angelo, who won easily by three quarters of a length, and Watercress.

Sir Hugo returned on 7 September for the St Leger at Doncaster.
He was third choice in the betting behind Orme, who had returned from training problems (he had allegedly been poisoned) to win the Eclipse Stakes and La Fleche, who had won the Oaks two days after her defeat in the Derby.
On a wet day in front of a huge crowd, Sir Hugo broke quickly but was then held up as Orme made the early running.
Orme was a beaten horse by the time the field turned into the straight when La Fleche went into the lead.
Sir Hugo produced a strong finish and ran on in "dogged fashion" to prove the best of the colts but could never get on terms with the filly and finished second, beaten two lengths, with Orme well beaten in fifth.

On 27 September Sir Hugo again challenged La Fleche in the £10,000 Lancashire Plate over one mile at Manchester Racecourse, but was never a threat and finished fifth of the eleven runners At Newmarket on 11 October he produced an excellent performance in defeat in the ten furlong Lowther Stakes, losing by a neck in a "close set-to" with El Diablo, to whom he was conceding fifteen pounds.
In the Limekiln Stakes over one mile at the Newmarket Houghton meeting, Sir Hugo was provided with a pacemaker named Flank March, but the tactic failed as he was well beaten, finishing third to Orme and El Diablo.
Sir Hugo began his three-year-old season on 4 May by running in the 2000 Guineas, a race which was considered very open after the withdrawal of the favourite Orme. He raced prominently, showing in third place at one stage, before finishing sixth of the fourteen runners behind Bona Vista
In the Derby on 1 June at Epsom Sir Hugo started at odds of 40/1 in a field of thirteen with La Fleche, who had won the 1000 Guineas being made the 11/10 favourite. He was ridden by the lightweight jockey Fred Allsopp, who had to carry more than 28 pounds of "dead weight" to make the stipulated 126 pounds. The weather was "gloriously fine" and the crowd was larger than usual. After several false starts which delayed the race by half an hour, the early running was made by Thessalian and Persistive with Sir Hugo just behind the leaders. The French-trained colt Bucentaur took the lead turning into the straight. Sir Hugo moved past Bucentaur a furlong from the finish and was strongly challenged by La Fleche. Cheered on by the bookmakers, Sir Hugo prevailed by three quarters of a length from the filly after a "desperate struggle", with Bucentaur a length further back in third Lord Bradford received £7,000 in prize money, but far more in winning bets, having backed Sir Hugo for the race at 100/1 before he ever ran. There were many observers who considered Sir Hugo's win to have been a "fluke". George Barrett, the rider of La Fleche, was criticised for giving the filly too much ground to make up while others drew attention to a collision between St. Angelo and Rueil at Tattenham corner which ended both colts' chances.
Sir Hugo was then sent to Royal Ascot where he started 4/6 favourite for the St. James's Palace Stakes over one mile. He led into the straight but was overtaken in the last quarter mile and finished third behind St Angelo, who won easily by three quarters of a length, and Watercress.
Sir Hugo returned on 7 September for the St Leger at Doncaster. He was third choice in the betting behind Orme, who had returned from training problems (he had allegedly been poisoned) to win the Eclipse Stakes and La Fleche, who had won the Oaks two days after her defeat in the Derby. On a wet day in front of a huge crowd, Sir Hugo broke quickly but was then held up as Orme made the early running. Orme was a beaten horse by the time the field turned into the straight when La Fleche went into the lead. Sir Hugo produced a strong finish and ran on in "dogged fashion" to prove the best of the colts but could never get on terms with the filly and finished second, beaten two lengths, with Orme well beaten in fifth.
On 27 September Sir Hugo again challenged La Fleche in the £10,000 Lancashire Plate over one mile at Manchester Racecourse, but was never a threat and finished fifth of the eleven runners At Newmarket on 11 October he produced an excellent performance in defeat in the ten furlong Lowther Stakes, losing by a neck in a "close set-to" with El Diablo, to whom he was conceding fifteen pounds. In the Limekiln Stakes over one mile at the Newmarket Houghton meeting, Sir Hugo was provided with a pacemaker named Flank March, but the tactic failed as he was well beaten, finishing third to Orme and El Diablo.
Sir Hugo