Ranking Jake Paul's boxing matches: Which knockout earned No. 1?

Jake Paul's unlikely turn from YouTube influencer to one of the biggest attractions in boxing continues on Friday when he steps inside the ring with his toughest challenge to date, former two-time unified heavyweight champion Anthony Joshua. Unlike in Paul's previous fights, he will not have a size, skill, experience or significant age advantage against the 2012 Olympic gold medalist.

Paul will be a +700 betting underdog, according to DraftKings. Few expect him to last more than a couple of rounds against Joshua, much less beat him. However, Paul has made a habit of silencing his naysayers by winning fights and putting on spectacle events.

Heading into his clash with Joshua, ESPN spoke to Paul (12-1, 7 KOs) about all of his professional fights and ranked each of them based on his performance, quality of opposition (considering his experience at the time of the fight), how the outcome affected his progression as a boxer and the overall magnitude of the event. Paul ranked the 13 fights as well.

1. Defeated Tyron Woodley by KO6 (Dec. 18, 2021)

After narrowly beating Woodley by split decision four months earlier, Paul was originally slated to face Tommy Fury on this night. However, Fury withdrew from the fight due to medical issues and Paul found himself face-to-face again with Woodley, who accepted the fight on short notice.

Many thought Paul had met his match in the former UFC welterweight champion. Considering that Paul had barely won in the first meeting, they expected Woodley to make the proper adjustments and hand Paul his first loss. Instead, Paul unleashed his biggest knockout, hammering Woodley with an overhand right in Round 6 that sent his rival crashing face-first to the canvas.

"I wasn't fighting very well before the knockout," Paul told ESPN. "But I did see the opening, and I wound up my punch as much as possible."

The fight was closely contested through the first five rounds, but Paul's continual use of a jab to the body slowly brought Woodley's hands down as the rounds progressed. Finally, Paul feinted a jab, saw his opponent's hands lower to protect the body and came crashing through with a right hand that knocked Woodley unconscious before he hit the canvas. This knockout is what made nearly everyone finally take Paul seriously as a boxer. To that point of his young career, he was seen as someone treating boxing as a side quest. But after the knockout, which ended up on several media outlets' knockout of the year lists, people realized that Paul wanted to make boxing his primary job.

"That was the biggest accomplishment and best feeling I've had after a fight, for sure," he said. "Being recognized for knockout of the year was such a special moment for me and something I never expected to happen."

Paul's ranking: 2

2. Defeated Nate Robinson by KO2 (Nov. 28, 2020)

In Paul's second pro fight, he faced Robinson, a three-time NBA slam dunk champion, in the co-main event of an exhibition match between Mike Tyson and Roy Jones Jr. in Los Angeles. The event took place at what was then known as the Staples Center, with no audience due to COVID-19 restrictions, and was broadcast via pay-per-view.

Paul was still widely viewed as just a YouTuber masquerading as a boxer, and a fight with a former professional athlete was widely expected to send him back to being a full-time social media influencer. Instead, Paul turned Robinson into a meme with a violent knockout that left him in an unconscious heap as more than 1.6 million viewers watched while awaiting the main event.

From the start, a disciplined Paul easily picked off Robinson's advances with a stiff jab, putting him down with a right hand in the opening round. In Round 2, the ineffective Robinson decided to charge at Paul, turning the fight into a brawl.

Bad idea.

Paul timed Robinson rushing in and caught him with a right hand, sending him down for a second time. A frustrated Robinson climbed to his feet and threw caution to the wind. But Paul stepped back and uncorked another right hand that caught Robinson flush and sent him down to the canvas for good. Rapper Snoop Dogg, who was on commentary for the broadcast, unleashed an "Oh lord!" into his microphone as Robinson's body crashed to the mat.

No count was necessary. Robinson was out cold, and Paul was standing tall.

"People thought the athlete was going to kill me," Paul said. "It turned out to be the eighth biggest pay-per-view of all time, and I had a highlight-reel knockout."

Paul's ranking: 1

3. Defeated Anderson Silva by UD8 (Oct. 29, 2022)

When idols become rivals -- that was the theme for Paul's sixth professional fight, in which he faced Silva, a former UFC middleweight champion, 22 years older than him. Paul remembers growing up as a huge fan of Silva during his legendary MMA run.

"[Anderson Silva] was my childhood idol and the only celebrity I met [growing up] in Ohio that I got his autograph and a picture with," Paul said. "It all came around full circle. That was an amazing night and good vibes all the way around."

Paul had previously fought two retired MMA fighters, Ben Askren and Woodley, twice, but Silva was different. His skills seemed more transferable to boxing, as Silva is widely recognized as one of the greatest strikers in UFC history. To make things even more interesting, Silva had defeated former WBC middleweight champion Julio Cesar Chavez Jr. by split decision a year prior, proving he could hold his own in a boxing ring.

The fight was a closely contested eight-round battle. Paul scored a knockdown in the final round to seal the win by scores of 78-73, 78-73 and 77-74. The fight was a lot closer than the scores indicated, though, and Paul said he had to dig deep to pull out the win.

"That was a great back-and-forth fight and the most sore I've ever been after a fight," Paul said. "It was a tough fight, and I was exhausted. Mentally, that was the deepest place I had to go to pull out a win, and I ended up dropping him in the last round. It was a special fight for me."

Paul's ranking: 3

4. Defeated Mike Tyson by UD8 (Nov. 15, 2024)

In terms of pure spectacle, Paul-Tyson is undeniably tops on this list. From the moment it was announced, the fight between an iconic heavyweight and one of the most popular influencers in the world captured the imagination of multiple generations. From hardcore Tyson fans to casual boxing fans who watch only because of Paul, everyone had an opinion on the fight. The 31-year age gap added intrigue, as some expected Tyson, despite being 58 years old, to summon his prodigious power to flatten Paul, while others believed the younger Paul, though far less experienced, would pull off the upset.

"In terms of entertainment, value, hype and the event itself, it is absolutely No. 1," Paul said. "But in terms of the actual fight, it's not high up there."

A whopping 60 million households streamed Paul-Tyson on Netflix and the fight brought in over 72,300 fans to AT&T Stadium in Arlington, Texas, with ticket sales of just over $18.1 million, which clocked in as the ninth-highest combat sports gate in U.S. history.

As for the fight itself, it was underwhelming.

It was evident from the opening bell that Tyson's advanced age made him unable to unleash the power that had made him a household name. Paul outboxed Tyson to a clear but uneventful unanimous decision, much to the chagrin of many watching, including Paul. "I wanted to go to war and had these visions of us both knocking each other down and we kept getting back up to fight," Paul said. "I was a little disappointed because I think that's what the fans wanted, too."

Paul's ranking: 5

5. Defeated Nate Diaz by UD10 (Aug. 5, 2023)

There was bad blood between Paul and Diaz long before they stepped into the ring. From their exchanges on social media to a backstage altercation at Paul's fight with Anderson Silva the previous year, the two fighters desperately wanted to square off. It didn't appear that a fight would ever come together due to Diaz being under contract with the UFC. However, after Diaz opted not to re-sign with the UFC when his contract was up in November 2022, and with Paul coming off a loss to Tommy Fury, the two sides came together and agreed to a 10-round fight at a catchweight of 185 pounds.

Diaz's cult hero status brought a hostile energy to American Airlines Center in Dallas. Every interaction between the two was contentious during fight week, as Diaz refused to fall for Paul's trash talk and was ready to throw down at any time, in any place.

Although Diaz had sparred with boxers, most notably undefeated two-weight champion Andre Ward, he was no match for Paul when they met. Paul had promised a knockout but had to settle for a wide unanimous decision and a fifth-round knockdown.

"He punches really soft and I just had to keep on punching him to win," Paul said. "I wish I could have knocked him out because his fans were still trying to say he won. I had high expectations to knock him out, but it ended up being an easy win."

Diaz absorbed some powerful punches but proved to be durable, refusing to give in no matter how far behind he was on the scorecards.

"He was just a zombie out there," Paul said. "What he's good at is getting hit, which is not fighting. But people love him for that, for some reason."

Paul's ranking: 10

6. Defeated Julio Cesar Chavez Jr. by UD10 (June 28, 2025)

In Paul's most recent fight, he took on Chavez in a cruiserweight fight. Although Chavez was 39 years old and far removed from his prime years as champion in 2011 and 2012, the son of boxing legend Julio Cesar Chavez was still perceived as a threat due to his pedigree as a former WBC middleweight titleholder and his power.

In front of a pro-Chavez crowd at the Honda Center in Anaheim, California, Paul dominated a lethargic Chavez from the opening bell, demonstrating his continued technical improvements with his footwork and jab.

"I'm proud of the Chavez fight," Paul said. "I think it was my sharpest fight overall, and being able to essentially starch someone like that who's a brick and veteran for eight to nine rounds, basically not taking much damage and just picking them apart."

The atmosphere may not have matched the unrealistic heights set by Paul's blockbuster fight with Tyson, but the buzz in the arena made it feel like a championship fight. And facing an opponent who had been a champion, Paul put together arguably his most complete performance.

Paul's ranking: 6

7. Defeated Mike Perry by TKO6 (July 20, 2024)

After Tyson experienced an ulcer flare-up that postponed their scheduled fight on this night, Paul needed a replacement opponent so his training camp wouldn't go to waste. He landed on another former UFC fighter, Mike Perry, who had gone on to become Bare Knuckle Fighting Championship's "King of Violence" champion.

Perry had left the UFC after going 2-4 from 2019-2021, but he found new life by taking off the gloves. He had amassed a 5-0 record with three knockouts in BKFC heading into the fight with Paul.

"He was on a winning streak and recognized as the king of bare-knuckle boxing," Paul said. "All these people said he was going to knock me out and talked about how tough he was. He was still in his prime, and I was able to stop him in a pretty vicious way."

Paul carried a significant size advantage -- Paul has a 76-inch reach, Perry, 71 -- and his stiff jab and big right hand helped him stop Perry in six rounds. The overmatched Perry was dropped with a chopping right hand in the first round, and another right hand sent him to the canvas in Round 2. Perry fought valiantly but was caught with a ferocious combination in Round 6 that ended the fight.

Although he was a betting favorite, Paul ranked the fight high on his list of favorites due to what he went through heading into it. He had fallen ill and had to push himself to get into fighting shape. He did not want to put a rescheduled fight with Tyson at risk with an underwhelming performance against the scrappy Perry.

"I don't get enough credit for that win," Paul said. "They tried to call him a retired MMA fighter, but no, he was a boxer who was crushing it in bare knuckle. People don't factor the change in opponent and how I had to lose 38 pounds in 28 days."

Paul's ranking: 4

8. Defeated Ben Askren by TKO1 (April 17, 2021)

After knocking out a fellow YouTuber (AnEsonGib) and a former NBA player (Robinson) in his first two pro boxing bouts, Paul wanted to prove that he could be a "real" fighter and set his sights on Askren, the former Bellator MMA and One Championship welterweight champion. The two traded barbs on social media before settling their differences at Mercedes-Benz Stadium in Atlanta in Paul's first pay-per-view main event. Many weren't convinced that Paul was serious about boxing; UFC CEO Dana White went on Tyson's podcast and said, "I'll bet $1 million that he loses this f---ing fight."

While Askren was a decorated MMA fighter, his base was wrestling and he had never been known for his striking. When the bell rang, it was apparent that he was in over his head.

"People tried to say that this 'real' fighter was going to go out and kill a YouTuber, and it ended up being easy work," Paul said.

In a matter of seconds, Paul put Askren on the end of his jab. Askren was clueless on how to get around it. With a little over a minute to go in the round, Paul flashed a jab and put a right hand behind it. Askren reached out to block the jab and was caught by the sweeping right hook, sending him crashing to the canvas. Askren got up but was on unsteady legs, and the referee rescued him from further damage, giving Paul a resounding stoppage win.

Paul's ranking: 8

9. Defeated AnEsonGib by TKO1 (Jan. 30, 2020)

Paul's first professional boxing match was against AnEsonGib, a YouTuber from Great Britain, on the undercard of Demetrius Andrade's WBO middleweight title defense against Luke Keener in Miami during Super Bowl LIV week. What was seen as little more than a novelty act took a turn for Paul when he knocked AnEsonGib down three times and won by first-round stoppage.

"That was the night I truly caught the boxing bug," Paul said.

He had come in well prepared, training in Big Bear, California, with Hall of Famer Shane Mosley. And while the fight itself was nothing special -- Paul laid waste to AnEsonGib with relative ease -- the attention it received made Paul realize he may have a new career path. After Paul's fight with AnEsonGib concluded, more than half of the fans at the Meridian at Island Gardens departed, despite there being a world title fight still to come. The attention was on Paul's pro debut, leaving Andrade and Keener to fight in front of a sparse crowd. Paul told ESPN that he knew right then that if he focused on developing as a boxer, he could be a game changer in the sport.

"It was surreal," Paul said. "I realized the draw that I had already become in boxing without even having a fight."

Paul's ranking: 9

10. Defeated Andre August by KO1 (Dec. 15, 2023)

In October 2023, Paul announced that he would begin going down the more traditional path in boxing and face fighters with pro experience rather than mostly MMA fighters, YouTubers and NBA players. He then headlined a non-PPV event put on by his own company, Most Valuable Promotions, in a fight with 10-1 boxer Andre August, who had nearly 40 rounds of pro experience.

"So far, my entire boxing career has been on pay-per-view," Paul said in a statement when the fight was announced. "But now it's about more than business. Now I want to build my experience in the ring against seasoned fighters."

Paul's desire to improve and be taken seriously as a boxer led to the fight with August, whom he finished with an uppercut in the first round, to improve to 8-1 with his fifth knockout. As an event, it was much more subdued than Paul's previous fights, but he was determined to prove himself to his skeptics.

"It was right before Christmas and people turned out to see me get a swift knockout in the first round against a fighter who was in his prime," Paul said.

Paul's ranking: 7

11. Defeated Ryan Bourland by TKO1 (March 2, 2024)

Following the first-round knockout of August, Paul was back in action less than three months later against another pro boxer with experience, ex-Golden Gloves champion Bourland. Once again, Paul opted to keep the fight off PPV and headlined a card he promoted in Puerto Rico, where he had relocated to live and train.

Paul made short work of Bourland, outlanding his opponent 24-3 and finishing the job with a flurry of punches in the opening round. Looking back, Paul said it was a solid performance but he wished he had gotten in more rounds as a professional fighter.

It would be the last fight for Paul on the "traditional" path to a world title. There were simply too many big opportunities that he couldn't turn down due to his significant drawing power.

Paul's ranking: 11

12. Defeated Tyron Woodley by SD8 (Aug. 29, 2021)

Before his fight with Askren, Paul was involved in a backstage confrontation with Woodley, which led to the former UFC welterweight champion calling out the social media star for a fight. Woodley, who had been a college wrestling teammate of Askren's and later trained with him in MMA, ridiculed Paul for facing opponents not known for their striking. After Woodley fought out his UFC contract, he pursued a fight with Paul, who readily accepted.

The fight headlined a Showtime PPV at Rocket Mortgage FieldHouse in Cleveland, and for the first time in his four-fight pro career, Paul was taken past the second round. Woodley rocked Paul in the fourth round with a right hand and kept the fight competitive, but Paul won a narrow split decision. Afterward, Paul gave his performance a C-, a grade he maintains today.

"My rhythm was off," Paul said.

For the first time, Paul looked vulnerable against an experienced fighter, and it nearly cost him.

Paul's ranking: 12

13. Lost to Tommy Fury by SD8 (Feb. 26, 2023)

Paul has suffered only one loss in his career, a split decision to boxer and reality TV personality Fury, half-brother of former heavyweight champion Tyson. The build-up was contentious, as they had exchanged trash talk for over a year. When they stepped into the ring in Diriyah, Saudi Arabia, in front of a house full of celebrities, Fury landed the cleaner punches and outworked Paul to win.

"Losing to Tommy Fury was definitely my lowest moment," Paul said. "The vibes were off heading into that fight, and it wasn't a fun experience overall. Even though it was a huge success in terms of pay-per-view, it's definitely the worst night of my career."

Paul did manage to score a knockdown in the eighth round, but it was not enough to salvage the night. For the first time, Paul watched his opponent have their hand raised in victory.