1850: three-year-old season
Although Voltigeur did not run in the spring of 1850 he was quietly fancied for the Epsom Derby with his support being particularly strong in Yorkshire where Zetland owned large estates and among the order of Freemasons of which he was a Grand Master. Shortly before the race, Zetland discovered that the colt's breeder had not made the correct entry payments and that it would cost £400 to run in the Derby. Zetland was determined to withdraw Voltigeur, but was persuaded to pay the entry fee after representations from his Yorkshire tenants, who explained that they had wagered heavily on the horse and faced ruin if he failed.
Voltigeur performed poorly in an exercise gallop shortly after arriving at Epsom, and was allowed to start at odds of 16/1 in a field of twenty-four runners. The start of the race was delayed after an objection was lodged against one of the runners, Diecoon. In an echo of the "Running Rein" affair of five years' earlier, the horse was only cleared to run after a veterinary surgeon examined him and confirmed that he was a three-year-old. Ridden by Job Marson, Voltigeur was settled in seventh place in the early stages before making his challenge in the straight. Inside the final furlong (0.20 km), Voltigeur took the lead ahead of the favourite Clincher and ran on strongly to win comfortably by a length. The 2000 Guineas winner Pitsford finished well to take second from Clincher in the last strides.
In September, Voltigeur returned to Yorkshire for the St Leger at Doncaster. He started favourite at odds of 8/13 against seven rivals. In the early stages, he was badly hampered as the other jockeys attempted to “box” him in a "ruck" against the rails, and Marson decided to change tactics. Instead of holding the colt up for a late run, he took Voltigeur into the lead at the turn into the straight and attempted to win from the front. In the closing stages Voltigeur began to tire and was caught in the last strides by Russborough, despite being hard ridden by Marson who had to use his spurs on the favourite. The judge declared a dead-heat, and with the owners of the colts failing to reach an agreement to divide the stakes, the two colts had to race again over the same course later that afternoon. Hill had planned to rest Voltigeur in his stable before the rematch but was advised by John Scott that if he did so he "might as well shoot him through the head" as he would stiffen up. Hill therefore kept Voltigeur walking round until he was called out for the deciding heat. At the second attempt, Marson was able to ride a waiting race on Voltigeur, tracking Russborough before moving ahead inside the final furlong to win "cleverly" by a length. The win, described by the Liverpool Albion as "one of the most memorable on record", provoked scenes of enthusiastic and prolonged celebrations by the Yorkshire crowd. Having run almost four miles (6.4 km) in the course of the afternoon, Voltigeur appeared the following day, and walked over to take the prize money in the Scarborough Stakes, when no other horses opposed him.
Despite his exertions, he turned out two days later for the Doncaster Cup in which he was the only horse to oppose The Flying Dutchman, the winner of the 1849 Derby and St Leger and undefeated in thirteen career starts. The Flying Dutchman, whose jockey appeared to be the worse for drink, set off at an exceptionally fast pace and Marson was able to bide his time on Voltigeur. In the straight Voltigeur moved up alongside the four-year-old champion and then pulled ahead to win by half a length in a huge upset.
The race inspired a poem from "The Druid" (W. H. Dixon), which was printed in Bell's Life and culminated with the stanza:
The ring stands pale. Forth speeds the tale, which many a doubt inspires
From east to west, from north to south, it glances o'er the wires.
From Richmond unto Middleham this message quickly passed
Your conqueror of conquerors has bowed his head at last.
After the race it was agreed that the two horses would meet again in a match race at York the following spring for a prize of 2,000 guineas, with each owner putting up half the sum.