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.
Jake Paul faces the biggest test of his boxing career on December 19. He will be facing Anthony Joshua, in a highly controversial professional boxing fight.
Paul’s post earlier this week that he would make an announcement about the event led to the fans believing the fight was cancelled.
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.
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5. Anthony Joshua vs Andy Ruiz Jr
The upset that occurred when Joshua faced Mexican heavyweight Andy Ruiz Jr. is ranked fifth.
This is the biggest upset in modern boxing history.
Joshua was initially scheduled to make his United States debut against Jarrell Miller. However, Miller tested positive for performance-enhancing substances and left the Brit with no opponent at short notice.
Ruiz Jr., fortunately for Joshua, accepted the call on late notice and filled in at short notice.
What followed…
2025-12-10 21:00:00
