The Biggest Horse Racing Upsets In History

Del Mar hosts the Breeders CupDel Mar hosts the Breeders Cup

The beauty of horse racing betting is its unpredictability. You get favourites and front-runners, but upsets happen. Horse racing history is littered with shock results and upsets - and there’s nothing we love more than an underdog victory… unless we lose money on it.

The thrill of seeing a last-minute surge is mind-blowing. But what are the biggest horse racing upsets of all time? Let’s look at the most memorable shockers in history. Here are those results that shook bookies and bettors alike.

Major Horse Racing Upsets

Memorial Stakes 1919 - The Upset by Upset

This is more about the horse that failed to win rather than the one that did… Upset by name and upset by nature.

The biggest favourite going into the race was Man O’ War - an undefeated prospect that was top of everyone’s list. However, Upset was the horse to upset the proceedings and serve up his one and only defeat.

Many consider Man O’War to be one of the best racehorses in the history of the sport - and this is certainly justified by the fact that in his 21-year career, he only ever lost this one race.

When the race was done, it was Johnny Loftus, the jockey, that took the blame for the shock, saying that it was his bad decisions and positioning that lost them the race.

Kentucky Derby 2009 - Mine that Bird

Another huge horse racing shocker came in 2009 at the Kentucky Derby, when Mine that Bird defied his 50/ odds to dash home to victory.

There were no major stand out favourites at the start of the race, but there were certainly some horses that were at the bottom of the list, Mine that Bird was one of them.

Punters and bookies had little faith in the horse… but he proved them wrong by becoming only one of none geldings to win the world-famous Kentucky Derby.

The horse, born and bred in Kentucky, had been sold for less than $10,000 and was trained by cowboy hat wearer Ben Wooley Jr. He wasn’t even expected to take part in this race and was only entered as a last-minute, spur of the moment decision. 

At the start of the race, he was at the back of the pack, well off the pace. However, jockey Calvin Borel rode Mine that Bird to an incredible recovery, flying past all of the others and ending up taking the win by six whole lengths.

This was such an unexpected turn of events that the commentator couldn’t even recall the horse’s name until he made his final surge.

Churchill Downs Home of the Kentucky DerbyChurchill Downs Home of the Kentucky Derby

The Breeder’s Cup 1993 - Arcangues

Although Arcangues wasn’t a failure of a horse, going in with a reasonable winning record, the bookmakers weren’t convinced and gave him long-shot odds of 133/1 for a win. 

At the last minute, Jockey Jerry Bailey was called in to ride the French horse at the $3 million race at Santa Anita Park.

He took the bull by the horns and ended up producing a breath-taking finish, catching up with front-runner Bertrando in the final stretch.

Had anyone bet just $2 on this result, they would have walked away with a $269.20 return, which is a race record that has never been matched since.

If we look at it logically, Arcangues had won both the Prix du Prince d’Orange and the JOhn Henry Handicap amongst others, so giving him odds of 133/1 was probably a bit on the generous side.

However, this horse had never run in the States and had never run on dirt - and his jockey didn’t even understand the trainer’s instructions and couldn’t even pronounce its name properly. It seems that the language barrier proved just a minor hurdle in this instance!


Belmont Stakes 2002 - Saravana

The big favourite of the race was War Emblem - who looked set to win the Triple Crown having already won the Preakness Stakes and Kentucky Derby. However, after an early stumble, his chances evaporated.

Then along came Saravana, with odds of 70/1. He started off well, staying near the front - and went on to outpace the rest, winning by half a length. He became the biggest long shot to ever win the Belmont Stakes.

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