Ultimate Upsets in Sports

In preparation for what could be one of the biggest sporting upsets of our generation when McGregor meets Mayweather, we've cherry picked a few of our favourite ever underdog victories in sport.

Wed, 16 Aug, 5:45 AM


Steven Bradbury

In what lives as one of the most iconic moments in Australian Sporting history, Steven Bradbury won gold at the men’s short track 1000m event at the Salt Lake City 2002 Winter Olympics.


Bradbury’s improbable run began in the quarter finals when he finished third behind home nation favourite Apolo Ohno and defending champion Marc Gagnon. With only the top 2 from the race progressing, Bradbury was handed a lifeline when Gagnon was disqualified for obstructing another racer.


In the Semi-Final and Final races of the event, Bradbury had been blessed with the luck of the Irish seeing all the competitors in both the races collide, crash and be unable to finish the race.


Bradbury coasted to a finals berth and eventually a gold medal.


The odds of all those events occurring are astronomically small. The universe clearly wanted Bradbury to don the Gold that night.


Leicester City

Make no Mistake. In a competition where the rich get richer and pull further away from the chasing pack, we may never see anything as incredible as what was witnessed with Leicester City. The Foxes triumphantly won the Premier League from under the noses of the perennial giants.


Not since 1994-95 when the Blackburn Rovers won it all have we seen someone from outside the traditional Top 4 powerhouses lift the trophy at the end of their campaign.


The Foxes were led by their charismatic Italian Manager, one Claudio Ranieri. The Team was spearheaded by misfit forward and cult hero Jamie Vardy. Vardy became notorious for his diet whilst on England duty consisting of Red Bull and cigarettes among other things.


The middle of the park was patrolled by Kante who has gone on to be a vital piece in Chelsea title winning team. The back four played an extremely vital role in anchoring this team that had built its identity on defence and counter attacking football. Robert Huth and Wes Morgan were outstanding down the stretch.


Leicester City’s 5000/1 odds to have undoubtedly changed the landscape of how sports betting is conducted moving forward.



James ‘Buster’ Douglas

Many of us probably weren’t around when this tale was written but in 1990 Mike Tyson lost to James ‘Buster’ Douglas. Douglas was a 42-1 underdog in the contest.


Tyson was slated to fight Evander Holyfield who was the number 1 contender at the time. Douglas was a lead up bout to the title fight with Holyfield.


23 days before the contest, Douglas’ mother passed away. Many believe this to be the motivation for the inspired performance witness from Douglas on fight night. Douglas’ uncle and trainer famously stated “I think, if anything, James will turn this into a positive. I really believe that”.


Douglas went on to land 129 more punches than Tyson with 5% more efficiency. Douglas’ use of his jab to control the fight was masterful.


Since this calamity for Tyson, the boxing world has not seen a bigger upset.


Where would McGregor rank in terms of all time sporting upsets if he defeats Floyd Mayweather? Would it be the biggest upset the boxing world has ever seen? It would surely rank highly given Conor McGregor has never had a professional boxing bout.



By Nik Hatzi

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