Every Jake Paul Opponent's Profile When They Fought Him

Updated: October 2026

Jake Paul's 12-2 professional record (7 KOs) across 14 fights is really a story told through other people's reputations. Every Jake Paul opponent arrived with a different résumé, a different kind of fame, and a different reason the fight mattered. Here is every opponent, profiled as they were at the moment they stepped in with him.

The Crossover Beginnings: AnEsonGib and Nate Robinson

AnEsonGib (January 30, 2020, Miami) was a fellow YouTuber — Paul's debut opponent and the only man on this list who shared his origin story. Paul stopped him in the first round, and the fight was widely treated as influencer spectacle rather than sport.

Nate Robinson (November 28, 2020, Los Angeles) was a former NBA player — a three-time slam dunk contest winner with genuine professional athletic pedigree, but no boxing background. Paul's second-round KO of Robinson was the viral moment that launched the entire enterprise.

The MMA Wave: Askren, Woodley, and Silva

Ben Askren (April 17, 2021, Atlanta) was a former MMA wrestler — an accomplished grappler whose striking had always been the weak point of his game. Paul knocked him out in the first round at 1:59, and the one-punch finish became an instant meme.

Tyron Woodley (August 29, 2021, Cleveland; December 18, 2021, Tampa) was a former UFC champion — the biggest MMA name Paul had faced to that point, and the first opponent with genuine knockout power in his hands. Paul beat him twice: a split decision in Cleveland, then a devastating sixth-round KO at 2:12 in the Tampa rematch.

Anderson Silva (October 29, 2022, Glendale) was an MMA legend — widely regarded as one of the greatest mixed martial artists ever, and unlike the others, a striker by trade. Paul's unanimous decision win over Silva was his most respected victory to date: eight rounds against a real fighter who could really punch.

The Reality Check: Tommy Fury and Nate Diaz

Tommy Fury (February 26, 2023, Saudi Arabia) was a reality-TV star turned pro boxer — the first genuine boxer Paul ever faced, and the man who handed him his first loss via split decision. Fury's profile was unique: famous from television, but with actual boxing fundamentals that proved decisive.

Nate Diaz (August 5, 2023, Dallas) was a UFC star — one of MMA's most beloved cult figures, famous for toughness and durability rather than one-punch power. Paul won a unanimous decision, outboxing a man who had built a career on refusing to go away.

The "Real Boxer" Phase: August and Bourland

Andre August (December 15, 2023, Orlando) and Ryan Bourland (March 2, 2024, Puerto Rico) were journeyman pro boxers — the first true professional fighters on Paul's record. Neither was a household name, and that was the point: Paul was rebuilding against real boxers, stopping both in the first round (August at 2:32, Bourland at 2:37).

The Spectacle Era: Perry, Tyson, and Chavez Jr.

Mike Perry (July 20, 2024, Tampa) was a bare-knuckle/MMA fighter — famously durable and violent, the kind of opponent expected to test Paul's toughness. Paul stopped him in the sixth round at 1:12.

Mike Tyson (November 15, 2024, Arlington) was a heavyweight legend — the most famous name Paul ever shared a ring with, decades past his prime but still carrying the aura of the baddest man on the planet. Paul won a unanimous decision.

Julio Cesar Chavez Jr. (June 28, 2025, Anaheim) was a former world champion — a real belt-holder from boxing's traditional ranks, and Paul's most credentialed boxing opponent. Paul's unanimous decision win was a legitimate boxing achievement.

The Heavyweight Reality: Anthony Joshua

Anthony Joshua (December 19, 2025, Miami) was a former heavyweight champion — a true elite heavyweight in his prime years, and by far the most dangerous opponent Paul ever faced. Joshua knocked Paul out in the sixth round at 1:31, breaking Paul's jaw in two places and ending the fight, and Paul's year, in brutal fashion.

FAQ

How many opponents has Jake Paul faced?

Paul has faced 13 opponents across 14 professional fights (he fought Tyron Woodley twice).

Who was Jake Paul's first real boxer opponent?

Tommy Fury, in February 2023 — Paul's first fight against a professional boxer, which he lost by split decision.

Who was Jake Paul's most famous opponent?

By global fame, Mike Tyson; by boxing achievement at the time they fought, Anthony Joshua.

Which Jake Paul opponent was a former world champion?

Julio Cesar Chavez Jr. was a former world champion, and Anthony Joshua was a former heavyweight champion.

Every Jake Paul opponent tells you where he was in his career when they fought. The YouTuber and the NBA player were about attention. The MMA fighters were about legitimacy. Fury was about truth. August and Bourland were about rebuilding. Tyson and Chavez Jr. were about scale. And Joshua was about the ceiling — the point where the story met reality.