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Read MoreRoyal Ascot is famous for its unexpected underdog victories, with some horses like Nando Parrado winning at staggering odds of 150/1 in 2020, showcasing the festival's unpredictability. Historical surprises like Flashman’s Papers and Fox Chapel further underline why betting on outsiders can pay off, as the combination of inexperienced runners and huge fields creates the perfect storm for shock results.
Every year, the Royal Ascot festival delivers world-class racing, unforgettable fashion and plenty of drama, but whilst most people look towards the favourites, there have been plenty of underdog winners throughout the years. Some of these unlikely winners have been the biggest betting shocks British Racing has ever seen, with some being recent and others being part of the excellent history of the festival.
Here at OddsMonkey, we are going to look at what some of the biggest odds winners were, why Royal Ascot produces shocks, and what those who take part in matched betting can learn.
The biggest price winner in Royal Ascot history was placed at a staggering 150/1. In 2020, Royal Ascot was staged behind closed doors during the pandemic, creating an unusual atmosphere that many believe contributed to a week full of shocks. None was bigger than Nando Parrado in the Coventry Stakes.
Trained by Clive Cox and ridden by Adam Kirby, the two-year-old was sent off at the price of 150/1 after only finishing fifth on its debut at Newcastle. Few gave him any sort of chance to win, as the field was packed with expensive and highly touted juveniles, but he travelled strongly throughout and made a surge at the end of the race. The result instantly entered Royal Ascot folklore and rewrote the books for the meeting’s biggest upset.
Another upset was caused by Flashman’s Papers, which occurred in 2008 throughout the Windsor Castle Stakes, and the horse was placed at a huge 100/1. Trained by Brian Meehan, the colt outran a field of far more favourable rivals to deliver one of the biggest surprises of the modern era.
Two-year-old races at Royal Ascot are typically known as difficult to predict, with many runners being inexperienced, whilst others will only be making their second start of their career. Flashman’s Paper is a clear case study for this point, as the outsider beat their competition to be one of the biggest underdogs in the history of the festival.
Before Nando Parrado and Flashman’s Papers, there was Fox Chapel in 1990, which managed to finish first with odds of 100/1. Being victorious in the Britannia Stakes, this race is typically known as one of the trickiest handicaps of the week, often featuring huge fields and razor-thin margins.
At the time, it was virtually unthinkable for a horse at triple-figure odds to win at the Royal Ascot, with elite trainers, top jockeys and heavily backed horses featuring here. Major upsets were relatively rare compared to ordinary handicaps, but Fox Chapel changed this perception forever.
Despite featuring some of the best horses in the world, Royal Ascot is a festival that many people look towards when value betting, as it can throw up some unlikely winners. Here are some of the reasons why the Royal Ascot festival produces so many shock results:
Royal Ascot is one of the toughest betting weeks of the year, but it also offers different opportunities for disciplined bettors. Rather than blindly backing the favourites, successful bettors can often focus on finding horses whose odds underestimate their chances.
Bettors can look for:
For those who are looking to learn more about horse racing, our matched betting blog is a great place to read up on horse racing and sports betting content.
The Royal Ascot festival is one of the biggest events in the horse racing calendar, and it requires plenty of preparation and research to make the most of it. At OddsMonkey, not only do we have blogs, but our betting calculators are essential to preparing yourself for the festival.
For more Royal Ascot content, users can check out the best Royal Ascot betting offers and our Royal Ascot matched betting guide on the site.

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