Epsom Derby’s Biggest Long Shot Winners (Including Three at 100/1 Odds)

Epsom Racecourse

The race in which legends are born and stallions are made has been the scene of some of the most memorable races and brilliant performances in the history of the sport. Many of these exceptional displays have been at least partially expected, others, not so much…

Well done if you managed to back any of this lot and, in the case of the top three, belated congratulations on your centenary.

6. 2020: Serpentine – 25/1

As ever, Aidan O’Brien was strongly represented in 2020, with no fewer than six runners making the trip over from Ballydoyle, including the mount of Ryan Moore, Mogul, Irish 2000 Guineas runner-up, Vatican City, and Hampton Court Stakes champ, Russian Emperor. With only a lowly maiden success to his name, and Emmet McNamara in the saddle, Serpentine was surely only in the field as a pacemaker. Wasn’t he?…

That certainly seemed to be the case, with the 25/1 shot immediately rushing up into the lead. Still six lengths clear as they made the turn for home, it became clear that a shock was afoot as the son of Galileo kicked fully 12 lengths clear into the straight. The jockeys in the pack finally did wake up, but all too late, as the son of Galileo comfortably held on for a runaway success.

With 50/1 shot Kahlifa Sat finishing second, followed by 66/1 outsider Amhran Na Bhfiann in third, this was a shock result all around. Any “Mystic Megs” out there with the foresight to place a £1 bet on the tricast were rewarded with a massive £55,977.83 payout.

5. 2017: Wings Of Eagles – 40/1

Shocking as the success of Serpentine was, it wasn’t the biggest Ballydoyle fuelled boil-over in recent times. That came in 2017, with the stunning last-gasp victory of Wings Of Eagles.

An unconsidered outsider, Wings Of Eagles was only the fourth shortest-priced runner from his yard. There had, however, been some promise in his previous runners-up finish in the Chester Vase and, despite being overlooked in the market, he rose to the big occasion in thrilling style.

In one of racing’s strongest examples of “like father like son”, Wings Of Eagles’ triumph was eerily reminiscent of the 2011 victory of his sire Pour Moi – albeit minus one of the most supremely confident celebrations in the history of the sport!

4. 1974 – Snow Knight – 50/1

It’s back to the 1970s for the only 50/1 winner on our list. 18 horses lined up, but according to the “experts” only three were in with a realistic chance. The Peter Nelson-trained Snow Knight certainly wasn’t one of them.

Snow Knight didn’t seem particularly motivated on the big day, depositing jockey Brian Taylor into the turf on the way down to post and fighting off all-comers before eventually being persuaded to enter the stalls. However, once underway, he was very keen to get on with things, marching straight into the lead, and remaining there. In comparison to others on this list, his frontrunning success most resembled that of Serpentine – with the addition of a bizarre musical accompaniment and commentary resembling that of a modern virtual race.

T1: 1913: Aboyeur – 100/1

The first 100/1 shot on this list is the winner of one of the most eventful editions in the 240+ year history of the race. The name Aboyeur loosely translates to “barker” – a strange choice for a thoroughbred, but one possible explanation is that the horse appears to have been barking mad.

Saddled alone and kept away from the other runners right up until the off, for fear of causing chaos, signs of lunacy then reared their head in the home straight, where Aboyeur veered all over the track before attempting to bite rival Craganour on the run to the line. Craganour came home in front, only to be disqualified by the stewards. Given Aboyeur’s antics, one can only guess what Craganour did to incur the wrath of the officials!

Aboyeur was owned by a group of notorious gamblers known as the Druids Lodge Confederacy – the men behind one of the most famous betting swindles in racing history. Biting horses and dubious connections aside, what this race is most remembered for is the death of Emily Davison.

A prominent suffragette, Davison opted to make her protest on the big stage. As the field rounded Tattenham Corner, Davison emerged from beneath the rails and walked straight in front of the King’s Horse, Anmer – ending her life, but securing a place in the history books and doing much to aid her cause.

T1: 1908: Signorinetta – 100/1

Next up, the only filly on our list – the remarkable, Signorinetta. The sight of a female tackling the males was a far more common occurrence in the early days of the race. A total of six fillies have, in fact, won the Derby, but the most recent of those victories came back in 1916.

Eight years before that 1916 success of Fifenella, it was Signorinetta who was showing the boys how it’s done – to the surprise of almost everyone. Everyone that is, apart from renowned poet and journalist Bosie Douglas who, in an impressive feat of clairvoyance, dreamt that the filly would win, and promptly placed a £5 bet (roughly £500 in today’s money) on her to do so. Not breaking a sweat in delighting Bosie, Signorinetta returned two days later to win the Oaks for good measure. They don’t make them like that anymore!

T1: 1898: Jeddah – 100/1

Sired by St. James’s Palace Stakes winner, and out of the 1000 and 2000 Guineas winning mare, Pilgrimage, Jeddah was both nicely named and incredibly well bred. His arrival into the world was nevertheless given a muted reception, with a groom describing him as, “the biggest and weakest” foal he had ever seen. By the end of the 1898 Derby, that description had improved to a far more impressive, “free-striding giant”.

That success was, however, completely unexpected, with the reported stunned silence which greeted his win suggesting there weren’t too many “Bosie Douglas” types lurking in the assembled crowd. Poignantly, almost as Jeddah was passing the winning post, his Classic winning dam was breathing her last breath.