Jake Paul faces the toughest test of his career by far by far when he takes on Anthony Joshua on the 19th of December.
The social media star turned boxer announced this week that he and Joshua will meet in a professionally-sanctioned bout in Miami, Florida.
Since he made the transition into the world of prizefighting critics have argued that Paul has consistently selected opponents that played squarely into his strengths as a fighter, namely either being MMA fighters with little to no boxing experience (Woodley, Diaz, Perry), or former boxers that are well past their fighting prime (Tyson, Chavez Jr).
And while he may be several years removed from his most recent reign as heavyweight champion, Joshua is neither of those.
If Paul is to shock the world when he takes on the 2012 Olympic gold medallist he will need to overcome significant disadvantages in both size and experience.
Stranger things have happened when heavyweight fighters strap on 10oz gloves, however. The 28-year-old will look to take inspiration from the biggest upsets in boxing history and we've compiled five of the most dramatic from the 21st century.
(16/1) - Dakota Linger defeats Kurt Scoby
Kurt Scoby will be a familiar name to boxing fans, particularly those who watched the rematch between Chris Eubank Jr and Conor Benn from the Tottenham Hotspur Stadium on Saturday night.
In that event Scoby took on undefeated super-prospect Adam Azim, and produced a valiant battling performance despite being outclassed by the British fighter prior to a stoppage in the final round.
Earlier in his career however, the former American football player turned boxer Scoby was a vaunted up-and-comer in his own right, winning his first 13 fights prior to a clash with Dakota Linger in 2024.
Scoby entered the fight as an overwhelming favourite but Linger survived an early onslaught to take control of the action and force the referee to stop the fight in the sixth of eight scheduled rounds.
(16/1) - Ezequiel Maderna defeats Karol Itauma
Unlike many of his contemporaries to feature on this list, Ezequiel Maderna is by no means an unheralded fighter.
The Argentine possesses a distinguished amateur pedigree that saw him represent his native country at the 2008 Olympics in Beijing and had challenged for the IBO super middleweight title after moving into the professional ranks.
By 2023 however, Maderna had lost three fights in a row for the first time in his career and was expected to pose little resistance when he fought Karol Itauma, elder brother of heavyweight contender Moses in a light heavyweight bout.
On the night that Moses made his professional debut, Maderna upset the apple cart against the elder Itauma, landing a right hand that dropped the younger fighter and left him unable to beat the referee's count.
(18/1) - Dante Jardon defeats Artem Oganesyan
Once tipped for great things at super featherweight, by the time Dante Jardon battled Artem Oganesyan he had become more of a gatekeeper, providing a stern test for talented up-and-comers in a variety of weight classes.
Put simply, a fighter expected to go on to challenge at the very highest levels of the sport would be expected to dispatch the all-action Mexican and avoid getting dragged into the kind of fight in which Jardon had proven to thrive.
Heading into their June 2023 bout, Russia's Artem Oganesyan had won all 13 of his professional bouts with 11 of those victories coming inside the distance.
His momentum was halted when the two met inside the ring, with Jardon getting his hand raised following ten rounds of action and claiming the NABF super welterweight title in the process.
(20/1) - Femke Hermas defeats Mary Spencer
A three-time world champion as an amateur, Mary Spencer wasted little time in building momentum after turning pro and moved to 7-0 in just over a year.
After claiming 'silver' belts with both the WBA and WBC, Spencer looked to add more silverware to her collection when she battled Belgian Femke Hermans for the IBO light-middleweight title in December 2022.
Already approaching 40 when she made the jump into the professional ranks, Spencer was being fast-tracked to a world title before she was comprehensively defeated by the 13-4 Lammens.
The pair rematched the following year with the odds now in the younger fighter's favour and she repeated the feat, claiming a majority decision win.
(20/1) - Jurmain McDonald defeats Evan Holyfield
Tasked with following in his legendary father's footsteps, Evan Holyfield faced an uphill battle from the moment he first laced up the gloves.
With his former cruiser and heavyweight champion father Evander watching on, Holyfield amassed an unbeaten record in his first nine fights, including a viral 16-second KO in his professional debut.
Throughout his early career Holyfield had rarely been tested by a serious opponent and a clash with 6-5 Missouri-based journeyman Jurmain McDonald was expected to be nothing more than a tune-up.
Towards the the end of the second round of their clash however 'The Shocker' lived up to his nickname as he sent Holyfield crashing to the canvas with a devastating right hand, handing him his first loss.
