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The worst horses in racing history - Five of the sport's famous flops

The Green Monkey has to be regarded as one of racing's biggest flops.

From dodgy Derby contenders and serial losers to the world's most expensive racing flop, we take a look at the five worst racehorses of all time.

Horse racing’s rich history is dominated by legends of the sport and horses such as Frankel and Black Caviar have attracted headlines on the front and back of newspapers all over the world. Both superstars ended their careers with their unbeaten record intact and they deserve their places in the sport’s hall of fame.

But what of the horses that have achieved legendary status as a result of their abysmal performances on the track? We take a look at some of the worst thoroughbreds in racing history.

First to achieve 100 consecutive defeats - Quixall Crossett

Quixall Crossett could be considered the worst racehorse in the history of British racing after he amassed 103 consecutive defeats in a far from glittering 11-year career.

An unwanted place in the record books was reserved for Ted Caine’s talentless operator after he became the first thoroughbred to lose 100 consecutive races at Southwell in July 2001. That came 10 years after his debut at Doncaster in 1990 and despite finishing second on two separate occasions; he never looked like winning any of his horrendous races.

Bizarrely, after his 100th consecutive defeat the gelding was allowed to race three more times and was hammered at odds of 500/1 on each occasion.

So bad he had a website dedicated to his woeful career, Quixall Crossett can claim to be the worst racehorse in the history of the sport.

Quixall Crossett loses again.

World’s worst winning racehorse – Quakeress

You’d think that a victory to your name would prevent you from entering the list of the world’s worst racehorses, but the mighty Quakeress demands a place in the mix.

After seventeen disappointing performances on the track, Quakeress stunned the world in February 2000 when she smashed the record for winning off the lowest handicap mark in British racing history.

Whereas the legendary Frankel finished his career on a mark of 135, Quakeress was rated a shocking 16 when she scored at odds of 25/1 for her stunned trainer and even more shocking was her victory in another race five days later.

Her climb to the top was short-lived, but despite never getting her head in front again, she goes down in history for her mind boggling success at Wolverhampton.

World’s worst Classic contender – Noddies Way

Racing’s incredible history is littered with sensational Classic winners from years gone by and the Epsom Derby has been won by the likes of Sea The Stars, Generous, Shergar and the incredible Mill Reef.

People will always wonder who the greatest Derby winner of all time was, but there is no denying that Noddies Way was the worst Classic contender in the history of the sport.

The jaw-droppingly poor horse took his chance in the 2003 Epsom Classic after his owner Wayne Cox left him in the world’s most prestigious race by accident and the bookies were happy to lay odds of 500/1 on the charge stunning racegoers with a Derby victory. Unsurprisingly, trainer John Panvert’s runner ended up 30 lengths behind the eventual winner, Sir Percy, after a typically diabolical performance.

It would be another two years before the horse broke his maiden tag at Lingfield, but he will always be remembered for his exploits at Epsom.

Noddies Way crawls home in the Epsom Derby. (Photo by Andrew Redington/Getty Images)

World’s biggest flop – The Green Monkey

Quakeress, Noddies Way and Quixall Crossett were all shocking performers but at least they were priced on their limited ability.

There were some stunned faces when breeding operation Coolmore parted with a whopping $16 million to purchase The Green Monkey in 2006 and the horse immediately became the world’s most expensive racehorse.

It was not long before it was clear he was also going to become the world’s biggest flop and connections were left scratching their heads when he retired after just three starts. With a measly $10,000 in prize money in the bank, The Green Monkey went to stud for $5,000 and left a lot of the Coolmore team red faced in the process.

The impressive beast was by no means the worst horse of all time, but he is certainly racing’s biggest disappointment.

World’s worst racehorse – Zippy Chippy

With a bridle nameplate that reads ‘Racing’s Biggest Loser,’ Zippy Chippy can rightly claim to be the worst racehorse of all time.

The hapless 21-year-old lost 100 consecutive races in the United States before he was retired in 2010 after scoring $30,572 in prize money.

It wasn’t all bad for Zippy, he finished second on eight occasions and was third 12 other times, but his lowest point came in 2000 when he inexplicably lost a 40-yard sprint to a minor-league baseball player. Jose Herrera powered clear of his rival to win their race by at least three lengths in what must have been a shock even to connections of the dreadful horse.

The superstar ended his career with legendary status and his name is all over fan clubs, message boards and forums. He even managed to find a place on People magazine’s list of the most interesting personalities.

Zippy Chippy, we salute you!

Zippy Chippy is turned over by a major league baseball player

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The worst horses in racing history - Five of the sport's famous flops

From dodgy Derby contenders and serial losers to the world's most expensive racing flop, we take a look at the five worst racehorses of all time.

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