As anyone with even a passing interest in betting knows, the sportsbooks tend to be bang on the money when it comes to analysing the chances of horses in a race, players in a match and teams in a game.

It’s a business model that sees them turn over millions of pounds/dollars/euros in revenue each year, and yet the sport has a habit of occasionally throwing the most unexpected results. You will read horse racing tips that leave no stone unturned in their pursuit of finding a winner or two on a card – form, trainer/jockey combination, suitability for the course and going, pedigree and preparedness are just some factors that can lead to success in predicting the outcome of an event.

But, even so, from time to time, things happen in a sport that simply could not be anticipated – as evidenced by this list of ten longshot winners.

Tipperary Tim (100/1)

One of the most eagerly anticipated races in UK sports betting is the Grand National. Held each year in April, this near four-mile slog is designed to crown the best steeplechaser in the business, who will navigate an Aintree course laden with tricky obstacles.

Generally, the market principles are those that head to the winners’ enclosure, but there have been five horses since the 1800s that have triumphed in the Grand National at odds of 100/1.

Tipperary Tim was the first back in 1928, and he was followed the year after by Gregalach and then Caughoo (1947), Foinavon (1967) and Mon Mome (2009).

20yo today! Happy Birthday MON MOME. After winning the Grand National & a 3rd in the Gold Cup, his retirement with Sarah includes parades at Aintree, Horse of the Year Show, & our Owners Parties. Videos – HoYS stables plus all dressed up & nowhere to go National day this year. pic.twitter.com/EkbG5UU4NE

— Venetia Williams (@VenetiaWRacing) April 29, 2020

Killahara Castle (200/1)

With one win in 22 starts, it’s not a huge surprise that Killahara Castle was not fancied in a mares’ novice hurdle race at Thurles in December 2017.

But she summoned up a sublime display to defeat the odds-on favourite True Self, powering into the lead before the final flight before running away to the line. This was a most unexpected turn of events…

Dandy Flame (200/1)

After finishing last by a country mile in his first career outing, it’s no shock that the bookmakers were downbeat on Dandy Flame’s chances in his next start at Wolverhampton.

Odds of 200/1 reflect the chances of an absolute no-hoper, but the Irish horse paid no heed – tearing up the formbook to win a maiden stakes race by over three lengths, to the bemusement of everybody.

Equinoctial (250/1)

Bookmakers’ odds of 250/1 give an outcome just a 0.4% chance of actually occurring via the law of implied probability.

So there was no way that Equinoctial could win a handicap hurdle at Kelso back in 1990… right!?
Wrong. Despite form figures of two PU-F-PU, Equinoctial ran like a champion to breeze home by three lengths and become – at the time at least – the longest-odds winner in UK racing history.

He Knows No Fear (300/1)

A befitting name, He Knows No Fear was a horse given basically no chance of winning a maiden race at Leopardstown in August 2020 on account of the fact that his form had been, there’s no other way to say it, terrible.

👀 ! We have a 300/1 shocker in the first race of the day on Racing TV as Sawbuck strikes at @punchestownrace for @codwyerracing and @C_G_ODwyer

Let us know if you were somehow on! 🙏🏻 pic.twitter.com/ySfROuIIFf

— Racing TV (@RacingTV) May 24, 2022

In a field of 15 horses, it seemed even more unlikely that an upset would happen, but He Knows No Fear lived up to his moniker and produced a dynamic late flourish to take the line ahead of the fancied Agitare.

Sawbuck (300/1)

It was earlier this year that Sawbuck equalled the record for the longest odds winner ever.
Conor O’Dwyer has trained Gold Cup winners in the past, but he would have had rather lower expectations for a horse whose best finish in his prior six outings was seventh – giving away 98 lengths to the various winners in that span.

But Punchestown was the setting for one of the greatest shocks in racing, as Sawbuck belied his form and asserted his dominance earlier before holding on to claim a memorable victory.
This pair of 300/1 winners remain the biggest in UK sportsbook records.