Biggest Racing Upsets Of The Past 20 Years

Horse racing is one of the most popular sports to bet on in the world. Nicknamed the Sport of Kings, it always offers spectators an exhilarating experience.

Whether you are an experienced gambler or a complete novice, there is a high chance that you had a flutter on the sport in the past – whether that be in person or on horse racing betting sites in the UK.

One of the best things about horse racing is when a complete outsider secures a shock win, throwing the formbook out of the window in the process.

Every time this happens, it creates headline news and reminds us that even the biggest underdogs always have a fighting chance of success.

Here are five of the very best racing upsets of the past 20 years. Some of them you are bound to remember!


If you are going to pull off an upset, you best do it on the biggest stage of them all – the Cheltenham Festival. That is exactly what Ebaziyan did in the Supreme Novices Hurdle in 2007.

After being out of action for 18 months, not a lot was expected from the horse and its rider Davy Condon. Ebaziyun was lumbered with 40/1 odds, making him the rank outsider.

Despite this, Condon rode him to a magical victory – eventually winning the race by three clear lengths. What a return to action it was!

Auroras Encore

The Grand National is always one of the highlights of the horse racing calendar and the 2013 iteration was one of the most memorable.

Going into the race, On His Own, ridden by legendary jockey Ruby Walsh was the favourite, closely followed by Colbert Station. Way down at the bottom of the betting slip was Auroras Encore ridden by novice Ryan Mania.

Despite being offered at odds of 66/1, Mania was not put off and managed to steer his horse to an extremely comfortable win.

Nando Parrado

Be honest, would you ever back a horse at 150/1? If you answered yes, we have a feeling you might be lying. Those were the odds that Nando Parrado was offered at during the 2020 Coventry Stakes – part of the Royal Ascot Festival.

Ridden by Adam Kirby, the horse remains the meeting’s biggest-priced winner to this very day. Anyone who did back him would have gone home very happy – but probably not as happy as Nando Parrado’s trainer, Clive Cox.

Cue Card

Although Cue Card would go on to become one of the best flat racers of his generation, back in 2010 the horse was a nobody.

Incredibly, Cue Card had just one race under his belt before making his Cheltenham Gold Cup debut in the Champions Bumper. No wonder he was numbered with odds of 40/1 by most bookmakers.

Despite no one backing the horse to triumph, he managed to do exactly that with Joe Tizzard riding him to victory in one the all-time great racing upsets.

Dandy Flame

We finish off our trip down memory lane, with our biggest racing upset so far. Strap yourselves in, because this one is unbelievable.

Winning your second ever race is impressive enough, but doing it at odds of 200/1 is incredible. That’s exactly what Dandy Flame accomplished in July 2016, winning as a rank outsider during a meeting at Wolverhampton.

On his debut at Windsor, Dandy Flame showed no signs of what was to come, finishing stone dead last. However, it was second time lucky for his rider Jose Santos who shepherded the horse over the line with a two and three-quarter length gap to second place.