Top 8 Boxing Upsets Of All Time

Written by Josh mccrohon

30 years ago, the world was stunned as 37-0 Heavyweight Champion, Mike Tyson lost his heavyweight titles to Buster Douglas in a fight which many saw as a warmup fight before Tyson before he went on to fight Evander Holyfield however Douglas had different plans as he knocked Tyson out in the 10th round. This may be the biggest upset in boxing history as previous to this, Tyson looked unstoppable. Upsets happen in boxing and when they happen, it’s a massive deal so today, I’ll be looking at the biggest upsets in boxing history.

8) Manny Pacquiao Vs. Oscar De La Hoya

This fight took place in 2008 and it was a non title bout however it got many people watching due to the fight being between two established names in the world of boxing. Manny Pacquiao was the underdog heading into this one due to De La Hoya being a naturally bigger man and this fight meant that Pacquiao had to move up 2 weight classes while De La Hoya moves down 1. Pacquiao was the underdog heading into ‘the dream fight’ but prevailed and got the win via TKO in the 8th round which many people didn’t see coming.

7) Lennox Lewis Vs. Hasim Raham

Heading into this fight, Hasim Rahman was a 20/1 underdog and was a boxer who many overlooked including his opponent, unified heavyweight champion, Lennox Lewis who was more concerned about a potential fight with Mike Tyson and even began negotiations but he lacked focus on this fight. As a result of this, Lewis got knocked out in the fifth round and Rahman would capture the heavyweight titles.

6) Wladimir Klitschko Vs. Corrie Sanders

Wladimir Klitschko losing isn’t the most common thing to ever happen, the man only lost 5 times in a 69 fight career which is pretty damn impressive however his second loss of his career came by KO in the second round. How did this happen? Corrie Sanders just dominated! He dropped Klitschko in the opening round with 33 seconds left before dropping him another three times. This was something nobody saw coming as at that time, Klitschko was 40-1 and set for big things. After this, Sanders lost against Vitali Klitschko the following year.

5) George Foreman Vs. Muhammad Ali

‘The Rumble In The Jungle’ is remembered as arguably being the greatest sporting event of the 20th century. Watched by apparently 1 billion people, the hype was real as undefeated and unified heavyweight champion, George Foreman was set to fight Muhammad Ali - a former heavyweight champion. Many expected Foreman to storm through Ali as only three of his 40 fights at that point, went the distance however Ali introduced the rope-a-dope tactic which is still amazing to this day. Ali becoming heavyweight champion in Africa is still one of the greatest boxing moments of all time.

4) Sonny Liston Vs. Cassius Clay

This is their first encounter where Liston was the heavyweight champion and Clay was a massive underdog. This fight was before the previous entry and Ali was an underdog heading Clay this one. This wasn’t because of Ali, this was because of Liston. Liston was seen as the most intimidating boxer at the time and some people actually believed Liston was a danger to the sport which made it more impressive when Clay won. However, another reason why Clay was a massive underdog was his fighting style, he kept his hands low and moved out of the way which many people predicted would be Clay’s downfall yet he went on to prove people wrong by making Liston quit on his stool in the 7th round.

3) Mike Tyson Vs. Evander Holyfield

In my opinion, Evander Holyfield is the greatest cruiserweight of all time and when he was set to fight Mike Tyson - many saw him as washed up and couldn’t get the job done. How wrong they were. This was a fantastic fight and unlike many predicted, Holyfield finished Tyson off in the 11th round after a gruelling fight.

2) Anthony Joshua Vs. Andy Ruiz Jr.

I still think this is absolutely crazy. Even though, I predicted a Joshua win, I gave Ruiz a chance, not a massive chance but still a chance and I was still stunned. After Joshua knocked Ruiz down with the uppercut and left hook, I knew it was the beginning of the end however it wasn’t. It really wasn’t. Ruiz came back and dropped Joshua. He then went on to become the unified heavyweight champion in the 7th round and he shocked the world. Many call this the biggest upset of all time and to be honest, an argument can be made. Ruiz wasn’t even supposed to fight Joshua - he was a replacement and he made the most of it.

1) Mike Tyson Vs. Buster Douglas

It’s no surprise that this is number one on the list, I did mention it in the intro. This fight took place in Tokyo and many expected it to be a typical Tyson victory however Douglas wasn’t willing to be another name on Tyson’s record and he put his name in the history books as he took out Tyson in the 10th round and became unified heavyweight champion while also having the biggest upset in boxing history.