Jake Paul’s Toughest Opponents Ranked: Easiest to Hardest

Updated: October 2026

Jake Paul’s toughest opponents tell the story of his career better than his record does. Across 14 fights and 13 different opponents, Paul has faced everyone from fellow YouTubers to a former unified heavyweight champion — and the difficulty curve has been anything but smooth. This ranking scores every opponent he has faced from easiest to hardest, based on their pedigree, their condition on fight night, and how much trouble they actually gave him. Number one will surprise no one. The middle of the list might.

How This Ranking Was Decided

This is a subjective ranking, and it weighs three things: the opponent’s overall combat pedigree, their physical condition and age on fight night, and the actual difficulty of the fight. A big name past his prime ranks below a lesser name in his prime. Knockout victims rank below men who took Paul the distance — or beat him.

The Ranking: Easiest to Hardest

13. AnEsonGib (Win, TKO1, Jan 2020)

A fellow YouTuber with no combat background. Paul’s debut opponent offered courage and nothing else. The easiest night of his career.

12. Nate Robinson (Win, KO2, Nov 2020)

A former NBA dunk champion, but a 5’9” basketball player trying boxing for the first time. The knockout was brutal and viral; the test was minimal.

11. Ben Askren (Win, TKO1, Apr 2021)

A genuinely elite MMA wrestler — and one of the worst strikers ever to headline a boxing event. Askren’s pedigree counts for something, but in a boxing ring he was a fish out of water, gone in a round.

10. Andre August (Win, KO1, Dec 2023)

A career professional boxer, which makes him a real test on paper — but Paul starched him in the first round. The “real boxer” label only goes so far when the fight lasts two minutes.

9. Ryan Bourland (Win, TKO1, Mar 2024)

Another career pro, another first-round demolition. Slightly more seasoned than August, but the result was the same story: overmatched early.

8. Mike Perry (Win, TKO6, Jul 2024)

A tough, durable MMA veteran who actually made Paul work for six rounds. Perry’s chin and pressure gave Paul rounds to solve — a genuine, if limited, challenge.

7. Nate Diaz (Win, UD, Aug 2023)

A UFC legend with an iron chin and endless cardio. Diaz took Paul ten rounds and never stopped coming, but he was a 38-year-old MMA fighter, not a boxer. Durable, dangerous in spirit, limited in the sweet science.

6. Tyron Woodley (Win, SD Aug 2021; Win, KO6 Dec 2021)

A former UFC welterweight champion with genuine one-punch power. Woodley pushed Paul to a split decision in their first fight — the closest Paul came to losing before Fury — before being knocked out cold in the rematch. Power earns him this spot.

5. Mike Tyson (Win, UD, Nov 2024)

The hardest name to place. On legacy, Tyson is the greatest opponent Paul ever faced. On the night — a 58-year-old man, twenty years past his prime — he was a moderate test who went the distance. Ranked here on the blend: still Mike Tyson, still dangerous for eight rounds, but a shadow of the legend.

4. Julio Cesar Chavez Jr. (Win, UD, Jun 2025)

A former world middleweight champion and a career boxer — the most technically schooled opponent Paul had beaten at the time. Past his best, but a real boxer with real fundamentals, and Paul handled him clearly.

3. Anderson Silva (Win, UD, Oct 2022)

A 47-year-old, yes — but a striking genius and one of the greatest mixed martial artists ever, still sharp enough to be dangerous. Paul’s decision win over Silva remains arguably the best victory of his career, and Silva gave him genuine problems across eight rounds.

2. Tommy Fury (Loss, SD, Feb 2023)

The first prime professional boxer Paul ever faced, and the first man to beat him. Fury’s movement, jab, and boxing fundamentals exposed the gap between Paul and a real pro. Close on the cards — Paul even scored a knockdown — but a clear step up in class.

1. Anthony Joshua (Loss, KO6, Dec 2025)

No debate. A former unified heavyweight champion, in his prime, knocked Jake Paul out in the sixth round and broke his jaw in two places. The gulf between this fight and everything else on the list is the story of Paul’s career: he can beat everyone below the elite line, and the elite line is very real.

FAQs

Who is Jake Paul’s toughest opponent?

Anthony Joshua, by a wide margin. Joshua knocked Paul out in the sixth round in December 2025 and broke his jaw in two places. Tommy Fury is a clear second.

Who is the easiest opponent Jake Paul has fought?

AnEsonGib, the fellow YouTuber Paul stopped in the first round of his January 2020 pro debut.

Has Jake Paul ever fought a prime boxer?

Tommy Fury in February 2023 was the closest — a young, active professional boxer. Anthony Joshua was an elite heavyweight. Both beat him.

Was Mike Tyson a tough opponent for Jake Paul?

On the night, moderately. Tyson was 58 and two decades past his prime, but his name, power, and presence made him a unique challenge. Paul won a clear unanimous decision.

Ranked easiest to hardest, the list reveals the central tension of Jake Paul’s career: dominance over everyone at his level, and two defeats against the only opponents above it. The comeback era will show whether that line can be moved.