5 worst losses suffered by UFC legends at the end of their careers

While each year sees plenty of UFC fighters hang their gloves up, unfortunately, many of them stick around for far too long. That's despite the best attempts of people like Dana White to convince them to step away.

The fact that so many UFC fighters hang on for too long has often meant that, over the years, a number of once-great fighters have suffered embarrassing losses in the octagon.

A lot of the time, these losses came against opponents who the aging star probably would’ve dealt with handily in their prime, making them even harder for the fans to stomach.

Here are five of the worst losses suffered by UFC legends at the end of their careers.

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#5. Donald Cerrone vs. Alex Morono – UFC on ESPN 24

It's unlikely Donald Cerrone would've lost to a fighter like Alex Morono in his prime

In his prime, Donald ‘Cowboy’ Cerrone – who finally retired earlier this year – was one of the most feared lightweights in the UFC, picking up huge wins over the likes of Melvin Guillard, Al Iaquinta and Eddie Alvarez during his tenure with the promotion.

However, while he holds a number of records, including the most post-fight bonuses in the promotion’s history as well as the most knockdowns, it’s safe to say that his final run before hanging up his gloves was hugely underwhelming.

Realistically, Cerrone’s durability was ruined by the fact that he was stopped by Justin Gaethje and Conor McGregor, but had he stepped away following his loss to ‘The Notorious’, it would’ve been a fitting end for him.

Instead, ‘Cowboy’ kept on fighting and reached his undoubted nadir in May 2021 when he was stopped by the unheralded Alex Morono in the first round of their welterweight bout.

Sure, ‘The Great White’ has gone onto a four-fight win streak since, but prior to his win over Cerrone, his record in the octagon stood at 7-4. More to the point, he’d only ever stopped one other opponent with strikes.

Essentially, it’s safe to say that in his prime, ‘Cowboy’ would never have fallen at the hands of a fighter on the level of Morono, meaning that this defeat was a red flag pointing him towards retirement.

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#4. Antonio Rogerio Nogueira vs. Ryan Spann – UFC 237

Ryan Spann's knockout of Antonio Rogerio Nogueira was a nadir for the Brazilian legend

Both the famous Nogueira twins – former UFC heavyweight champ Antonio Rodrigo Nogueira and his brother, light heavyweight contender Antonio Rogerio Nogueira – are often accused of hanging on for too long before retiring.

However, while ‘Big Nog’ only fell to high-level contenders such as Roy Nelson and Fabricio Werdum before stepping away from the octagon in 2015, the same cannot really be said for his brother.

After surprising everyone in 2018 by rolling back the years to knock out Sam Alvey in Sao Paulo, ‘Lil Nog’ probably should’ve hung up his gloves on a high point. Instead, he returned eight months later to face off with relative newcomer Ryan Spann at UFC 237.

At the time, ‘Superman’ had just one victory in the octagon to his name – over the unheralded Luis Henrique in his debut with the promotion – and his record of 15-5 hardly suggested he was a blue chip prospect to watch.

However, when faced with the slow and plodding Nogueira, Spann looked like a world-beater. He needed just two minutes to destroy the former PRIDE legend with punches, silencing the Brazilian crowd in the process.

Given that ‘Lil Nog’ had been known for his pinpoint boxing in his prime, it was hard to see him easily dismantled on the feet in this way. While Spann has done relatively well for himself since, the loss remains a bad one on this legend’s record.

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#3. Rashad Evans vs. Dan Kelly – UFC 209

Rashad Evans found himself outpointed by the unheralded Dan Kelly towards the end of his career

Former UFC light heavyweight champion Rashad Evans suffered a pretty terrible end to his career with the promotion, losing a total of five bouts in a row before hanging up his gloves in 2018.

However, while nobody would ever bemoan defeats to the likes of Glover Teixeira and Anthony Smith, seeing ‘Suga’ clearly outpointed by Dan Kelly in March 2017 was remarkably disappointing for a number of different reasons.

Firstly, it was the first time Evans had lost to anyone but an elite-level competitor, with Kelly unranked at 185lbs at the time, during his tenure with the UFC.

Secondly, some fans were expecting Evans’ first drop to 185lbs to reignite his career. Unfortunately, that wasn’t the case at all, as he actually looked more slow and plodding than he’d done in even his worst losses at 205lbs.

Thirdly, unheralded Australian Kelly, despite an outstanding background in judo, was not the most explosive athlete in the promotion, meaning that it was hard not to imagine Evans dispatching of him with ease in his prime.

Instead, ‘Dad Bod’, as he was lovingly christened by MMA fans, largely picked the former champion apart with his boxing, keeping him at the end of his punches for most of their bout.

When Kelly was then knocked out by Derek Brunson, a fighter who was very similar to prime Evans, in his very next trip to the octagon, it only made the whole thing even harder for fans of ‘Suga’ to stomach.

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#2. Shogun Rua vs. Paul Craig – UFC 255

Shogun Rua found himself on the wrong end of a serious beatdown from Paul Craig

While the other fighters named on this list have all hung up their gloves – at least in the UFC – former light heavyweight kingpin Mauricio ‘Shogun’ Rua is still part of the promotion’s active roster, although he doesn’t have a future fight booked right now.

The Brazilian, who is widely considered a genuine all-time great of the 205lbs division, has arguably been past his prime for the best part of a decade now. In fact, he probably hasn’t been at his best since suffering a severe knee injury following his initial light heavyweight title win back in 2010.

However, in recent years, he’s reached a real nadir, with his lowest point undoubtedly being a TKO defeat to Paul Craig in November 2021.

It’d be unfair to label ‘Bearjew’ a bad fighter – the Scotsman is actually ranked in the top 10 at 205lbs right now and could’ve claimed an unlikely title shot had he beaten Volkan Oezdemir – but the truth is that despite his excellent grappling skills, he’s the kind of fighter that Shogun would’ve destroyed had they met in say, 2005.

Unfortunately for the Brazilian, though, the fight actually took place in 2021and saw Craig thoroughly dominate the former champion, taking him down with relative ease and eventually forcing him to submit to a series of heavy punches to the head.

Whether Shogun ends up suffering an even worse loss in the near future remains to be seen. For now, it’s fair to say that this defeat stands out as his most disappointing.

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#1. B.J. Penn vs. Ryan Hall – UFC 232

BJ Penn would probably have dealt with Ryan Hall in his prime - rather than being submitted easily

Few UFC legends fell quite as hard as B.J. Penn did towards the end of his storied career. ‘The Prodigy’, who was once considered the best pound-for-pound fighter on the planet, ended his time with the promotion after a seven-fight losing streak.

However, while there was no shame in the Hawaiian losing to the likes of Nick Diaz, Frankie Edgar and Yair Rodriguez, his later defeats were definitely disappointing, with one standing out more than the others.

In his prime, Penn was a remarkably dangerous fighter for a number of reasons, but primarily, he was an almost impossible opponent for grapplers.

Not only did he possess a world-class grappling game in his own right, with a Brazilian jiu-jitsu black belt and phenomenal skills from the guard, but he was also a strong enough wrestler to defend most takedowns. He also possessed some of the sharpest boxing skills in MMA.

However, by the time 2018 came around, while Penn’s old skills were still there to an extent, they appeared to be fading fast, as did the explosive athleticism that made his takedown defense so impervious.

When he was faced with Ryan Hall at UFC 232, then – a rare example of an almost pure grappler in the modern-day octagon – it was easy to imagine that a prime ‘Prodigy’ simply would’ve stuffed his takedowns and dealt with him on the feet handily.

Instead, a far slower Penn was unable to really deal with ‘The Wizard’ and his unorthodox attacks. H fell victim to a rolling heel hook, something that would almost certainly not have happened years before.

The loss represented rock bottom for ‘The Prodigy’. Although he would fight one more time, in another loss to Clay Guida, it’s the loss to Hall that stands out as being truly bad.