Michael Bisping names the five biggest flops in the UFC's history

A former WWE wrestler makes the list alongside a former boxing world champion and a fighter who got knocked out by Jake Paul.

The UFC is viewed as the cream of the crop in the mixed martial arts world.

Lifelong MMA fighters work for years just to get a chance in Dana White's octagon - but it doesn't always go to plan.

For every Conor McGregor, there's an unfortunate fighter such as CM Punk. Former middleweight champion Michael Bisping spoke on his Youtube channel about the biggest flops in UFC history.

5) Kimbo Slice

Michael Bisping's first flop on the list was Kimbo Slice.

Despite his heavy hands and his entertaining style, Kimbo never quite lived up to the hype once he entered the UFC.

He was invited onto The Ultimate Fighter: Heavyweights in 2009 and was selected as the first overall pick by Quinton 'Rampage' Jackson. However, Slice was eliminated from the competition by Roy Nelson in his first fight.

After the Ultimate Fighter, Slice competed twice more in the UFC. He picked up a victory against Houston Alexander via decision, before losing his third fight in the company to Matt Mitrione.

Slice ended his UFC career with a record of 1-2. He sadly passed away in 2016.

4) CM Punk

The former WWE and current AEW star swapped the four-sided wrestling ring for the octagon in 2014, but he didn't enjoy a successful transition.

Back in 2014, Phil Brooks (CM Punk) announced he had signed a multi-fight contract with the Ultimate Fighting Championship.

But his first fight within the company wouldn't come until 2016 when he faced Dana White's Looking For A Fight competitor - Mickey Gall.

Gall, an impressive grappler, totally dominated the fight in Punk's debut. He took the former wrestler down with ease and sunk in the rear-naked choke in the first round.

Punk's next fight was against the man that Gall had beaten for the right to face Punk - Mike Jackson. Now Jackson was more of a kickboxer, but the fight went a similar way, Jackson being in control of the fight and winning a decision.

This result was later overturned to a no-contest after Mike Jackson tested positive for Marijuana, so Punk's UFC record is 0-1-0 (one no contest).

3) James Toney

James Toney is a former Ring Magazine Fighter of the Year, a multiple-time world champion and a pound for pound superstar
James Toney is a former Ring Magazine Fighter of the Year, a multiple-time world champion and a pound for pound superstar

James Toney was a fantastic boxer. He was a former Ring Magazine Fighter of the Year, a multiple-time world champion and a pound for pound superstar. But his success in the boxing ring didn't translate over to MMA.

Toney attended UFC 108 - Evans vs Silva at the MGM Grand in 2010. He began speaking to Dana White about the possibility of fighting in the UFC and it was later announced that he would sign a multi-fight deal with the company.

The former IBF middleweight champion was pitted against now UFC Hall of Famer Randy Couture. Couture secured an early takedown and finished the fight with an arm-triangle choke.

Toney was later released and he finished his time in the UFC with an 0-1-0 record.

2) Mirko Cro Cop

Unlike the others on the list, Mirko Cro Cop has more than one victory in the UFC - he actually has five. However, with his record outside the UFC being 21-4-2, fans expected more from the Croatian kickboxer.

Cro Cop signed with the UFC in 2006 after his contract with Pride had expired. He was placed in a bout against Eddie Sanchez, and the former kickboxing standout knocked Sanchez out within a round.

One year later, Cro Cop was placed in a number one contender fight with Gabriel Gonzaga in the United Kingdom. Gonzaga would shock the world by knocking the Croatian out with a Cro Cop-Esque head kick in round one.

He would then lose to Cheikh Kongo before taking a hiatus from the UFC competition. Cro Cop would return at UFC 99 in Germany, and compete until 2011 when he finally retired from the octagon.

Mirko Cro Cop ended his UFC career with a record of 5-6 - a drastic difference from his 21-4-2 record before entering MMA's biggest proving ground.

1) Ben Askren

Ben Askren is one of the greatest wrestlers of this generation. He was part of the 2008 US Olympic wrestling team, and his success transferred to MMA in promotions such as ONE and Bellator.

Askren would win the welterweight title in the aforementioned organisations and he was undefeated for over a decade - before he entered the UFC.

The former Dan Hodge trophy winner was traded to the UFC in return for Demetrius Johnson, and it was announced that Askren would be taking on welterweight staple Robbie Lawler in his debut.

And his debut would go according to plan. Askren sank in a bulldog choke on the former welterweight champion and Herb Dean would call a controversial ending to the bout within one round.

Next up for Ben Askren was Jorge Masvidal. After plenty of back-and-forth between the two, Masvidal would put an end to the talking on fight night.

The man known as 'Gamebred' raced into the centre of the cage and knocked Askren out with a flying knee after five seconds - the fastest knockout in UFC history.

Askren would later face a fellow grappler, but more submission-heavy Demian Maia in 2019. He would add another loss to his record and announce his retirement a month later. His UFC record would end at 1-2.

Since then, Askren has fought Jake Paul but it didn't last long with the YouTuber knocking Askren out in the opening round.

READ MORE: Fury vs Ngannou can be a mixture of boxing, MMA and five-minute rounds, says heavyweight

Latest news