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The Worst Boxing Match Ever and Other Legendary Disappointments

Richard Janvrin by Richard Janvrin, June 02, 2025

Dubbed “The Fight of the Century” between Floyd Mayweather Jr. and Manny Pacquiao

Boxing is an intriguing sport. Sometimes, bouts can be built up for months or years, and at times, the time between the rumors, announcements, and bout can lead to expectations growing so high that the actual fight cannot meet the hype. Other times, some fights are flat-out, just not good.

Fans can feel frustrated, cheated, or downright angry when this happens, especially when they put their money on the line at the best betting sites for boxing.

Below, I’ll examine 10 of the most disappointing boxing matches. I’ll start with the No. 10 bout and conclude with the worst boxing match ever.

10. Tyson Fury vs. Francis Ngannou (2023)

For this fight, it was really the fans of Tyson Fury who were disappointed. Remember, Fury, a reigning heavyweight champion, was a massive favorite and expected to handle Francis Ngannou, a former UFC star, relatively easily. However, Ngannou knocked Fury down. Fury escaped with a split decision in a bout that could be considered most boring boxing match ever. Sure, he probably expected to win, but the lack of preparation was evident, serving as a reminder to never take any opponent for granted.

9. Canelo Álvarez vs. Gennady Golovkin I (2017)

While the bout itself wasn’t disappointing, as Canelo Alvarez and Gennady Golovkin delivered some impressive action, the outcome was overshadowed by the final result. Golovkin appeared to get the win by landing more effective punches. However, in the end, judge Adalaide Byrd had a scorecard of 118-110, resulting in a draw. For many fans, the controversial scoring turned what could have been a classic into a candidate for the worst boxing fight ever in terms of outcome and frustration. That decision has overshadowed an excellent fight, leaving fans massively disappointed. Not only that, but Alvarez also tested positive for clenbuterol, which is “abused generally by bodybuilders and athletes for its ability to increase lean muscle mass and reduce body fat,” per the DEA. Alvarez was then suspended, and the second bout was eventually canceled.

8. Muhammad Ali vs. Antonio Inoki (1976)

We all know who Muhammad Ali is. As for Antonio Inoki, he was a Japanese wrestling star, and this was billed as “The War of the Worlds.” However, it was viewed as one of the most embarrassing moments in Ali and his cornermen’s careers. Many even consider it the worst boxing match ever. The rules of the bout were odd, and Inoki spent a lot of time lying down and kicking Ali. Fans booed throughout it, and it ended in a draw. Not only that, but Ali dealt with some leg injuries. Inoki and Ali became friends later, and this helped to form the rise of mixed martial arts in the country. That said, this is a fight all Ali fans would like to forget and could be considered the worst boxing fight ever.

7. Oscar De La Hoya vs. Felix Trinidad (1999)

Anytime a fight is billed as “The Fight of the Millennium,” the hype is already sky-high. At first, the fight lived up to that, with De La Hoya outboxing Trinidad. However, as the fight went on, De La Hoya began to adopt a more defensive stance and retreat, and he believed he had won. Well, Trinidad didn’t back down. When the fight went to a decision, Trinidad was given the win. This stunned De La Hoya and fans alike. He started off with what appeared to be a winning bout, but just didn’t keep that pressure up. It wasn’t so much the worst boxing match ever, but extremely confusing.

6. David Haye vs. Wladimir Klitschko (2011)

Leading up to this fight, David Haye talked a big game. This was a heavyweight unification clash against Wladimir Klitschko, and he promised to take him down. However, when the bell rang, Haye’s strategy was far different than what we believed it would be. Shoot, he wore a t-shirt that showed Klitschko decapitated. Haye went on to lose via unanimous decision, and he blamed it on a broken toe. He did a good job building up the fight, but his performance made for a disappointing bout that had quite an eyebrow-raising build.

5. Bernard Hopkins vs. Roy Jones Jr. II (2010)

The second meeting between these two, Bernard Hopkins and Roy Jones Jr., came 17 years after the first one. However, at the time, I’m not sure fans were exactly excited for it as they were both well past their prime and, well, the fight showed. There were a lot of pauses, clinching, and other fouls. If there were any fans hoping for something explosive, it was far from that. In fact, there were only 150,000 pay-per-view buys. Dan Rafael from ESPN called it an “abomination” and a “horrible fight,” calling for both of them to retire. Trust me: Rafael wasn’t the only one to think this was the worst boxing fight ever

4. Lennox Lewis vs. Mike Tyson (2002)

The lead-up to Lennox Lewis and Mike Tyson in 2002 led fans to believe something crazy was about to happen. There were insane press conferences, animosity, and fans were promised something massive. However, by the time the fight happened, Tyson was not in his prime whatsoever, and Lewis was able to control the fight and finish it with a knockdown, winning by KO in the 8th round. This wasn’t a battle between two legends; it was one legend admired by many getting dominated and a reminder that his best days were behind him.

3. Riddick Bowe vs. Andrew Golota I (1996)

Heading into this bout between Riddick Bowe and Andrew Golota, fans expected something more out of Bowe. Golota dominated most of the fight. However, he kept delivering low blows. Despite many warnings from the referee, he kept going and was disqualified. This led to fans rioting inside Madison Square Garden, and devolving further into brawls. This was far from the most boring boxing match ever. However, this can easily be considered the worst boxing match ever, and I wouldn’t argue.

2. Mike Tyson vs. Evander Holyfield II (1997)

There’s really not a lot to say about this one: Tyson bit Evander Holyfield’s ear off.

The fight was stopped, Tyson was disqualified, and this completely ruined what should’ve been one of the best battles between two great boxers.

Disappointed? Yeah, to say the least.

1. Floyd Mayweather Jr. vs. Manny Pacquiao (2015)

In the modern era, the fight between Floyd Mayweather and Manny Pacquiao was meant to define an entire generation of the sport. There were plenty of complications leading up to it, including failed negotiations. The hype for this festered and festered for a long, long time. Finally, when the fight arrived, it didn’t live up to expectations.

Mayweather was defensive, per usual, and neutralized Pacquiao. This was a low-risk chess match of sorts between these two.

This was the type of fight that drew in millions of casual fans who may not have been as aware of Mayweather’s style. This was a massive moment to help boxing become even more popular, but it led to what many called the most boring boxing match ever after a half-decade of build.

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