Boxing’s Biggest Crossover Contests

In recent years, the boxing world has seen a surge in crossover matchups that have captured the imagination of fans worldwide. One of the most talked about of these bouts in recent times takes place soon as the polarizing Jake Paul battles it out with former World Heavyweight Champion Mike Tyson. Despite the latter being 58 years of age, many still feel that he has a puncher's chance of eliminating the Problem Child, with the bookies making him a narrow 6/4 underdog for the upcoming clash.

These crossover bouts have become somewhat commonplace in the world of boxing over the last half a decade or so, sparking debates about the future of the sweet science. Whether you love them or hate them, one certain thing is that such contests rake in bucket loads of cash. But which contests are considered the biggest so far in this relatively modern phenomenon? Let's find out.

Floyd Mayweather vs. Conor McGregor

The buzz surrounding Paul vs. Tyson is reminiscent of the groundbreaking Floyd Mayweather vs. Conor McGregor fight in 2017. This bout was a landmark event, not just for its sheer audacity but also for its financial success. Back then, the brash Irishman was arguably the most famous sports star on the planet, reeling off highlight-reel knockouts against former pound-for-pound king Jose Aldo and Eddie Alvarez to become the first simultaneous two-weight world champion in UFC history.

Rather than defending either of his titles, however, the Notorious clamoured for a fight with arguably the greatest boxer of all time, Floyd Mayweather. The Dublin-born icon claimed that nobody inside the UFC was on his level, and with the amount of money he had earned for the company, he had earned the right to seek out this life-changing fight against Money May. Ultimately, Dana White agreed, and the bout was penned for August sending the planet into a state of disbelief.

Perhaps one of the most surprising aspects of “The Money Fight” was just how much people believed in McGregor to get the victory. Due to punters chasing steam – a term given to drastic and somewhat unnatural odds movements – and lumping on the Irishman in their droves, his betting odds were slashed down to 3/1. Because the two-weight UFC world champion was making his professional boxing debut and facing off against the greatest of all time no less, the odds on his victory should have been closer to 25/1 or even higher.

On fight night, McGregor had a positive start, landing several big shots on the former five-weight world champion. In the end, however, his gas tank failed him once again, just as it had done many times before inside the Octagon. Mayweather would begin to pour it on in the late rounds, ultimately picking up a tenth-round knockout victory and sealing his record-breaking 50th win.

Logan Paul vs. Floyd Mayweather

Following in these footsteps was another high-profile matchup: Logan Paul vs. Floyd Mayweather. Logan – like his brother Jake – rose to fame through social media before diving into the boxing world. He twice fought with British social media presence KSI, drawing the first before losing the second on home turf in Los Angeles. However, both those bouts did huge pay-per-view numbers, and Mayweather wanted a piece of the pie.

Unlike the boxing great's previous bout with McGregor, this contest was less about competition and more about entertainment, yet it still succeeded in captivating a massive audience. With Paul being much younger and bigger than his more experienced opponent, many thought he may have a chance of landing some big shots on 'Money'. But over the years, much better fighters than the Maverick have tried, and failed.

The contest ultimately wasn't scored and was contested under exhibition rules, with no fighter able to secure a knockout. But despite that, it was yet another huge commercial success.