5 former UFC champions who suffered embarrassing losses after leaving the promotion

#2. Chuck Liddell – former UFC light heavyweight champion

Chuck Liddell's decision to return from retirement didn't pay off at all

Once considered the UFC’s poster boy and their biggest star, former UFC light heavyweight champion Chuck Liddell was renowned for his brutal knockout power and killer instinct for years.

However, after he lost his title to Quinton Jackson in 2007, things quickly went downhill for ‘The Iceman’. Sure, there were some flashes of the “old” Chuck, most notably in his wild victory over Wanderlei Silva. But by 2008, it was clear that his time at the top was up.

Liddell suffered three straight losses against Rashad Evans, Mauricio Rua and Rich Franklin, all by knockout. That was enough for UFC President Dana White to coax him into retirement in mid-2010.

However, part of Liddell’s retirement package involved an office job with the UFC. It was essentially a token of the promotion’s appreciation for his years of hard work. When the UFC was bought out by Endeavor in 2016 and began to embark on cost-cutting measures, Liddell’s job was one of the first things to go.

This left ‘The Iceman’ needing some money. Sadly, that meant a return to fighting, something that everyone but Liddell seemed to know was a bad idea. Incredibly, in 2018 it was announced that Liddell would be facing his old rival Tito Ortiz, who he’d beaten twice in the UFC. The bout took place under the Golden Boy MMA banner.

The fight was immediately condemned by MMA fans worldwide. Nobody thought the near-50-year-old Liddell ought to be fighting. They were quickly proven right.

Liddell appeared to be moving through treacle during the fight and quickly succumbed to a first-round knockout loss at the hands of his rival. The loss was painfully embarrassing for ‘The Iceman’, particularly given the rivalry between him and Ortiz. It came as no surprise that he announced a return to retirement shortly after.

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#1. Tyron Woodley – former UFC welterweight champion

Tyron Woodley's loss to Jake Paul was embarrassing - even if it earned him plenty of money

Whether or not Tyron Woodley’s first loss following his UFC departure could be considered embarrassing is probably up in the air. That depends on your thoughts on the fighting skills of his opponent.

However, considering Woodley held the UFC welterweight title as recently as 2019 and had only ever lost to elite fighters like Kamaru Usman and Colby Covington, it’s hard not to shudder at the thought of his recent loss to YouTube star Jake Paul.

Sure, there were plenty of caveats surrounding the fight. Firstly, it took place in the boxing ring. While Woodley had been renowned for his knockout power in the octagon, he reached the top of the UFC primarily by using his wrestling.

Secondly, ‘The Chosen One’ was substantially outweighed by Paul in the fight. He also hadn’t really been at his best for over two years by the time the two men stepped into the ring. In fact, he hadn’t won a fight since his 2018 victory over Darren Till.

And thirdly, Woodley did at least take ‘The Problem Child’ the distance. He even stunned him with a big right hand at one stage.

Jake Paul vs. Tyron Woodley by the numbers. pic.twitter.com/79jXbE1qzm

— ESPN (@espn) August 30, 2021

However, Woodley’s loss was still hard to stomach, particularly for UFC fans who’ve become a little sick of Paul’s anti-MMA act. They were desperate to see someone shut him up for good and were left disappointed when Woodley failed to do so.

Was the loss as embarrassing as the ones suffered by fighters like Sylvia and Liddell? Perhaps not, but it was still a tough watch. No former UFC champion should lose to a YouTuber, after all.