The top 5 biggest upsets in boxing history as Jake Paul attempts to steal the crown against Anthony Joshua

In just a few weeks’ time, Jake Paul looks to pull off the biggest upset in the history of combat sports when he takes on former champion, Anthony Joshua.

On December 19, Jake Paul takes on by far the toughest test of his career when he clashes against Anthony Joshua in a highly controversial professional boxing bout.

Earlier this week, Paul worried the fans when he posted that he was going to make an announcement regarding the event, which led fans to believe the fight would be canceled.

Fortunately, though, the fight is still on and ‘The Problem Child’ is now just a few weeks out from attempting to pull off the biggest upset in the sport’s history.

With that, let’s take a look back at the five biggest upsets the sport has ever seen, including several fights including Paul’s former opponent, Mike Tyson.

5. Anthony Joshua vs Andy Ruiz Jr

Potentially controversially coming fifth on this list is the upset that happened when Joshua fought Mexican heavyweight Andy Ruiz Jr.

Although there have arguably been bigger upsets in the history of the sport, this is one of the biggest in the modern history of boxing.

Joshua was originally set to make his debut in the United States against Jarrell Miller but Miller tested positive for performance enhancing drugs, leaving the Brit without an opponent on extremely short notice.

Fortunately for Joshua, though, Ruiz Jr accepted the late-notice call and stepped in on short notice.

What proceeded was one of the craziest turn of events, ever, as despite being knocked down early in the fight, Ruiz Jr responded with knockdowns of his own, scoring a seventh round KO.

4. Evander Holyfield vs Mike Tyson

Throughout their respective careers, Evander Holyfield and Tyson were linked to fight each other on several occasions, but plenty of issues continued to step in the way of the blockbuster.

After ‘Iron’ Mike returned to the sport following years in prison, he quickly put together several big wins, putting him back into title contention.

And despite being ordered to fight Lennox Lewis after winning the WBA title, the heavyweight went on to fight Bruce Seldon, which subsequently opened the doors for a fight against Holyfield.

At that point, Holyfield was considered to be past his prime after retiring from the sport due to a misdiagnosed heart condition before returning years later.

Heading into their fight, Tyson went in as a huge favorite but despite a fast start, it became clear that Holyfield was the stronger of the two.

A few rounds in, Holyfield found himself out-boxing Tyson, as ‘Iron’ Mike couldn’t make the correct adjustments to get back into the fight.

Midway through the fight, Tyson was cut by an accidental headbutt, which seemed to throw him off for the rest of the rounds. And in round 7, he suffered a surprise knockdown.

Then in round 10, Holyfield once again cracked Tyson and seemed to have him out on his feet, but the sound of the bell saved him. However, it didn’t save him for long, as in the opening moments of round 11, Holyfield poured it on Tyson, resulting in a stoppage and one of the biggest upsets ever.

3. Leon Spinks vs Muhammad Ali

After a win over Earnie Shavers, Muhammad Ali decided to fight 1976 Olympic Gold medalist Leon Spinks in an undisputed heavyweight title fight.

At that point, Spinks was only seven fights into his professional boxing career following his extremely successful Olympic career.

What followed was a huge shock as Spinks dethroned Ali, picking up the split decision win, becoming the undisputed champion in just his eighth professional fight.

2. Cassius Clay vs Sonny Liston

After winning the heavyweight world titles in 1962, Sonny Liston was widely regarded as the most terrifying fighters in the world by the end of 1963.

By that time, Liston had already defeated eight of the top 10 ranked contenders at heavyweight, with seven of those victories having come by knockout.

And then in 1964, he was matched up against Cassius Clay, before he changed his name to Muhammad Ali. At that time, Clay was still relatively unknown to the masses and he had already almost suffered several setbacks in his career.

In his fight before fighting Liston, Clay was almost beaten by Henry Cooper after being knocked down by a left hook and wasn’t regarded as much of a challenge for Liston.

What proceeded will forever go down in history as one of the biggest upsets ever, and what saw the birth of Muhammad Ali as many came to know him.

After six rounds, Liston decided he could no longer continue and the fight was called, seeing Clay announced the victor.

1. Mike Tyson vs Buster Douglas

Tyson vs Buster Douglas is widely regarded as the biggest upset in the history of boxing because of Tyson’s dominance at the time.

Going into their fight in 1990, Tyson was the undefeated and undisputed heavyweight champion and he was continuing to grow in power and popularity.

Douglas was ranked number seven in the division and had mixed success at that point. Despite Tyson being feared by the majority of the world, early in the fight, Douglas showcased that he was not scared of ‘Iron’.

After an extremely back-and-forth fight, Douglas was dropped in round eight but made it to the bell. When round nine began, Tyson attempted to pour the pressure on Douglas to finish the fight, but he was countered and his eye ended up closing completely from the damage he sustained.

And then in round 10, the unthinkable happened when Douglas landed a heavy combination, dropping Tyson for the first time in his career. He was subsequently counted out, suffering the biggest upset loss in the history of the sport.