For elite-level fighters, tasting defeat on the big stage is one of the bitterest pills to swallow, particularly when there is no disputing you have come up second best.
But a hefty paycheck can certainly soften the blow.
While the headlines and history books point to whoever’s hand was raised – or perhaps whoever’s hand deserved to be raised – over the years a number of pay-per-views stars have thickened their wallets despite coming unstuck in high-profile super-fights.
With the help of Betsperts, Mail Sport has taken a look at the 10 richest losers in boxing history, based on the earnings of defeats suffered in fights which generated over a million PPV buys worldwide. Another caveat is the figures only go back to 2009.
A certain British heavyweight features on the list, while there is also room for a very famous one-fight novice…
For every winner in one of boxing’s high-profile super-fights there also has to be a loser
10. Joseph Parker – £6.7million per loss
In the highest-grossing fight of his career to date, Parker took on unified heavyweight champion Anthony Joshua in March 2018 and was soundly beaten in front of 78,000 fans at Cardiff’s Principality Stadium.
The New Zealander, who brought the WBO title into the contest, failed to get close to AJ over 12 rounds and was therefore on the wrong end of a unanimous decision points loss.
Yet for his troubles, he took home a whopping £6.7million base purse.
Parker has not been involved in an event of such magnitude since, though, and another big heavyweight scrap is further from his grasp than ever after a knockout defeat against Joe Joyce last year.
8=. Caleb Plant – £8.3million per loss
When Plant stepped into the ring with Canelo Alvarez, the No 1 pound-for-pound fighter on the planet at the time, in November 2021 the primary aim was to etch his name into the history books as an undisputed super-middleweight champion.
In the end the American failed to do that, with Canelo instead turning the screw after 11 highly-competitive rounds and forcing a stoppage in Las Vegas to capture a fourth title out of four at 168lbs.
Plant’s memorable encounter with the top attraction in boxing is believed to have generated 800,000 PPV buys in the US alone – and that meant he earned a career-high £8.3million.
That figure was dwarfed by Alvarez, nevertheless, who swept up an estimated £32million from his 57th career win.
After suffering his first defeat, Plant got the better of Anthony Dirrell 11 months later before a one-sided points loss against David Benavidez came in March.
America’s Caleb Plant has made over £8million for every defeat of his professional career
8=. Canelo Alvarez – £8.3million per loss
While he has long cemented a legacy as one of the greatest to ever do it, Canelo hasn’t always had his own way in these lucrative mega-fights.
The Mexican superstar has come up short twice in his storied career – and both were comprehensive defeats.
Floyd Mayweather first boxed rings around a 23-year-old Canelo in September 2013, cruising to what should have been a shut-out points win if not for an inexplicable 114-114 scorecard from C.J. Ross.
As boxing’s undisputed PPV king at the time, Mayweather collected an astonishing £33million for his latest triumph, with Canelo settling for a not-too-shabby £5million.
The latter was not beaten again for close to a decade, slumping to his first defeat in almost nine years against world light-heavyweight champion Dmitry Bivol in May of last year, paying the price for stepping up in weight and taking on a true 175lbs master.
Nevertheless, Canelo still pocketed roughly £12million for that shortcoming, meaning he has generated an estimated £16.65million for his two career defeats (£8.3million per loss).
7. Miguel Cotto – £9.6million per loss
Puerto Rico’s Miguel Cotto slides in at number seven after pocketing a generous £9.6million for every loss throughout his professional career (since 2009, that also had over 1million PPV buys).
His defeats against Floyd Mayweather Jr, in May 2012, and Manny Pacquiao, in November 2009, helped the former light middleweight claim such lucrative numbers.
Against Pacquiao, Cotto was dealt a crushing TKO defeat in the opening minute of the 12th round. For his troubles, he took home around £11.5million
For his clash with ‘Money’ Mayweather, Cotto put his WBA ‘Super’ light middleweight title on the line in-front of a packed out crowd at the MGM Grand.
He would lose via unanimous decision but there were debates as to whether that was a fair score. Cotto, multiple times, had Mayweather against the ropes in the fight.
He took home just below £8million following the bout – which saw his career earnings (for losses) amount to £19.5million.
Miguel Cotto (L) suffered a unanimous decision defeat when he fought Floyd Mayweather
6. Gennady Golovkin – £10million per loss
The only fighter able to dispute a defeat on this list is Golovkin, who was on the wrong end of a highly contentious points decision when he met Canelo for a second time in September 2018.
Having got the better of their first clash one year earlier and been forced to settle for a controversial draw, GGG was left seething once more after another enthralling battle with his old adversary in Sin City, which went Canelo’s way on the scorecards.
After hearing the judges’ verdict he stormed out of the ring in anger, adamant that his arm should have been raised, and in his case a fight purse of £4million may not have been a sufficient consolation.
Canelo went toe-to-toe with his bitter rival for a third and (hopefully) final time back in September, cruising to a more comfortable points victory in what proved a largely uneventful contest between two fighters perhaps beyond their peaks.
Golovkin took home a meatier £16million for that encounter, meaning his two career losses brought him £20million.
4=. Wladimir Klitschko – £10.8million per loss
Ukrainian heavyweight Klitschko only has one defeat which meets the parameters of this list, but it was enough to earn him a whopping £10.8million.
In April 2017, the legendary boxer faced off with Britain’s Anthony Joshua in-front of a post-war record crowd of 90,000 at Wembley Stadium.
In their thrilling bout, which was settled in the 11th round, Klitschko was handed the first stoppage defeat of his career since 2004 – a record that stretched 13 years.
Joshua ensured victory on the night after he delivered a huge upper-cut that left the Ukrainian dazed, confused and heading towards back-to-back defeats.
Anthony Joshua delivered a crushing blow on Wladimir Klitschko to secure a TKO win in 2017
4=. Andy Ruiz Jr – £10.8million per loss
When Jarrell Miller failed multiple drug tests in the lead-up to a showdown with Anthony Joshua at Madison Square Garden in June 2019, the unified heavyweight chief turned to Ruiz as a last-ditch replacement ahead of his eagerly-awaited US debut.
Largely due to his obscure profile and unathletic physique, Ruiz was an overwhelming outsider in with a ripped, undefeated champion in AJ – and that made his stoppage victory in New York all the more astonishing.
Six months later the Mexican defended his three world championships in a money-spinning rematch out in Saudi Arabia, and this time around a more danger-wary Joshua ducked and weaved his way to a routine win on the scorecards.
Ruiz earned £10.8million for his role in that Middle East battle, but after slumping to a second career defeat he admitted to spiraling into a cycle of over-eating and depression.
3. Anthony Joshua – £22million per loss
Joshua picked up his first win since December 2020 at the start of this month, after triumphing over American counterpart Jermaine Franklin.
The British boxer was left desperate to secure a win, and revitalise his career, after he suffered back-to-back defeats to Oleksandr Usyk in September 2021 and August 2022.
In their first encounter, Joshua took on the Ukrainian at the Tottenham Hotspur Stadium. Expectations of the Brit had been high but, in the end, the task proved too much for him.
He lost via unanimous decision and walked away from the bout with £10million in his back pocket before agreeing to a rematch with the heavyweight.
When they faced-off again, it was an almost identical outcome for the Brit. Instead of a unanimous decision, he lost via split decision, as Usyk bested him across 12 rounds of action. For the rematch, Joshua pocketed £34million – averaging out to £22million per loss.
Anthony Joshua (R) was dealt back-to-back defeats by Ukrainian boxer Oleksandr Usyk
2. Conor McGregor – £25million per loss
Unlike any other fighter on this list, McGregor has only climbed through the ropes of a boxing ring on one occasion – and it earned him an incredible £25million.
The UFC superstar ventured into boxing for a unique crossover bout with Mayweather in August 2017, which generated unprecedented levels of attention as the two outspoken kings of their respective combat sport locked horns both verbally and physically.
McGregor may well have got the better of the pre-fight trash-talk bonanza, however it was Mayweather who made his boxing expertise count when they settled their feud at Nevada’s T-Mobile Arena.
The five-weight world champion bettered his professional record to a perfect 50-0, while McGregor took his mammoth pay check and headed back to UFC.
1. Manny Pacquiao – £60million per loss
And, at top spot, it’s none other than Filipino boxer-turned-politician, Manny Pacquiao.
Despite only having two defeats that qualify him for this list, Pac-Man easily trumps the rest with his £60million-per-loss earnings.
The first fight which saw the Filipino fighter net a lucrative sum, despite losing, was his fourth encounter with Juan Manuel Márquez in Las Vegas on December 8, 2012.
Manny Pacquiao (R) and Floyd Mayweather’s fight is the highest-grossing bout in history
Having suffered defeat in their three previous fights, Mexico’s Marquez put a stop to that streak with a huge knockout victory over Pacquiao in the sixth round. Despite the defeat, the Filipino walked away with £20million.
Just three years after that defeat, Pacquiao would then take part in the ‘Fight of the Century’ against Floyd Mayweather.
The bout against his American rival would go on to be the highest-grossing fight in the sport’s history – generating somewhere between £300 million and £400 million.
Pac-Man would pocket £100million of that, while Mayweather took £144million, to bring his average earnings-per-loss to a cheeky £60million.
