The biggest cross-over fights in recent boxing history

As Jake Paul prepares for his sensational clash with Anthony Joshua in Miami on December 19, the spotlight is once again fixed on the wild and lucrative world of crossover boxing.

It’s a genre that blends showmanship, celebrity culture, and combat in a way that splits opinion yet commands enormous audiences.

With fans already studying the Joshua odds ahead of the blockbuster bout, it’s the perfect moment to look back at the fights that built this strange new era.

Logan Paul vs KSI (2018 & 2019)

The rivalry that launched a movement. When Logan Paul and KSI first collided at Manchester Arena in 2018, with the bout ending in a draw after Jake beat KSI’s brother Deji earlier in the night, the idea of YouTubers selling out stadiums was almost unthinkable.

Their rematch in Los Angeles a year later — this time as professionals — proved influencer boxing was not a fad, but in fact a phenomenon. The success of both events laid the foundations for today’s crossover era.

Conor McGregor vs Floyd Mayweather (2017)

The original super-crossover. When Conor McGregor — MMA’s biggest star — stepped into a boxing ring in Las Vegas against a 49–0 Floyd Mayweather, the hype was immense.

McGregor impressed early on, but Mayweather’s experience prevailed, ending the fight in the 10th round. With over 4 million pay-per-view (PPV) buys, it remains one of the biggest combat sports events in history. Mayweather, who was comfortably leading on the scorecards when the stoppage came, admitted to being surprised by McGregor’s ability: "He was a lot better than I thought. But I was the better man. I guaranteed everybody this would not go the distance. Boxing's reputation was on the line."

Floyd Mayweather vs Logan Paul (2021)

Another match-up that few believed would happen. Yet millions watched as Logan Paul, with a huge size advantage but minimal experience, went eight rounds with one of the greatest defensive boxers of all time.

Despite the hype, the fight itself was a huge disappointment, with Mayweather landing just 43 punches and Paul less than 30.

Those hoping to see Mayweather end the fight with a knockout, or Paul cause one of the biggest upsets of all time, made their feelings clear with a ring of boos at the end of the subdued fight.

Mike Tyson vs Jake Paul (2024)

Perhaps the most surreal crossover of all. A 57-year-old Tyson returning to face Jake Paul drew huge debate and even bigger numbers.

After a postponement for Tyson’s health scare, Paul won via unanimous decision at AT&T Stadium. Netflix viewership peaked at 65 million, proving crossover boxing’s unrivalled reach.

For casual fans exploring boxing betting odds, this fight was a prime example of how crossover matchups captivate audiences far beyond traditional boxing circles.

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Crossover boxing may irritate purists, but it has redefined modern combat entertainment. These fights have sold millions of PPVs, pulled in vast streaming numbers, and introduced entirely new demographics to the sport.

And with Paul vs Joshua on the horizon — perhaps the biggest spectacle yet — one thing is sure: Crossover boxing isn’t slowing down. In fact, it’s only getting bigger.