Jake Paul and Tyron Woodley stand for photos at the press conference for upcoming boxing match.

YouTube sensation Jake Paul turned pretty much everyone's head when he entered the world of professional boxing. Even if you didn't know much about him, even if you didn't like him, the move was interesting enough to grab your attention. And then the former Disney star started winning. Not just winning, but backing up his smack talk with impressive knockouts. Now his upcoming fourth professional boxing match will be his toughest test, as the pay-per-view boxing event Jake Paul Vs. Tyron Woodley pits "The Problem Child" against mixed martial artist Tyron Woodley, who is known for throwing powerful punches.

The bad blood between Tyron Woodley and Jake Paul seemed to start before Paul's previous fight against Woodley's longtime friend and training partner Ben Askren. Woodley got into it with Paul's cornerman, fellow boxer J’Leon Love backstage ahead of the pay-per-view main event. After Paul's victory, Woodley called Paul out for padding his record with fights against non-boxers. Not that Woodley is a boxer either, but even Paul acknowledged that this fight is "a step up," saying he wants to challenge himself against someone with Woodley's knockout power. So let's take a look at what we know about Jake Paul Vs. Tyron Woodley, including how to watch.

Jake Paul speaks at press conference ahead of boxing match with Tyron Woodley

The Fight Is Set For August 29 In Jake Paul’s Hometown Of Cleveland, Ohio

Jake Paul Vs. Tyron Woodley is set for Sunday, August 29 at the Rocket Mortgage Fieldhouse in Cleveland, Ohio. And as if Paul didn't already have millions of fans following him from around the world, he'll also have the home-field advantage. Paul was born in Cleveland, growing up in nearby Westlake. The fight broadcast is set to start at 8 p.m. ET for an eight-round contest that will be fought at an agreed-upon 190 pounds catchweight, which means it falls between two official weight classes.

The boxing ring is shown from a distance during a Showtime event

The Fight Will Air Live On Showtime PPV

Jake Paul vs. Tyron Woodley will air live on Showtime PPV and will be available for purchase through Showtime's website or app. You do not need a subscription to Showtime to watch the PPV. The price for the fights hasn't yet been announced. Showtime's most recent PPV featured Jake Paul's brother Logan Paul vs. Floyd Mayweather for a cost of $49.99, but Showtime typically carries a higher price tag for higher-caliber boxing. If you want to attend the event live in Cleveland, Ohio, tickets go on sale July 22.

Jake Paul screams like a madman

Jake Paul Has Knocked Out All Of His Previous Opponents

Three professional fights, three early KOs. Jake Paul made his debut against fellow YouTuber AnEsonGib in January 2020. The fight was declared a victory for Paul at 2:18 in the first round. Paul's second fight was against the NBA's Nate Robinson — no stranger to a good brawl himself. In December, Paul beat Robinson by knockout at 1:24 of Round 2. At least Robinson made it to Round 2. And on April 17 in Atlanta, Paul made quick work of Ben Askren, winning by technical knockout at 1:59 of Round 1.

Tyron Woodley looks intensely away from the camera.

Tyron Woodley Is A Former UFC Champion

Tyron Woodley, widely considered one of the most dangerous punchers in UFC history, held the UFC Welterweight Championship from 2016-2019, with four title defenses in that period. His MMA record is 19-7-1, with 14 of those 19 wins coming from early finishes. However, after losing the welterweight belt, Woodley suffered three more losses. In 2021, it was reported that he parted ways with UFC. Ben Askren still thinks his teammate is the man to beat Jake Paul, as after his own defeat, Askren said Woodley is "a significantly better boxer than I am."

Jake Paul points a finger at Tyron Woodley.

The Loser Of The Fight Has To Get A Tattoo Of The Winner's Name

If money, pride and career advancement weren't enough, there's something a little more personal on the line come August 29. After a multi-million-dollar wager fell through, Jake Paul made Tyron Woodley a new offer during their recent press conference.

Let’s make a new bet — if I beat you, you have to get ‘I love Jake Paul’ tattooed on you. But if you beat me, I get ‘I love Tyron Woodley’ tattooed on me and you have to post it on your Instagram feed.

They shook hands, so it's official. Let's go!

Floyd Mayweather talks on Jimmy Kimmel Live

Floyd Mayweather Is Helping To Train Tyron Woodley

It may be Tyron Woodley’s professional boxing debut, but he’s learning from the best. Floyd Mayweather Jr., who accumulated a perfect 50-0 professional boxing career, met with Woodley for training, Woodley told FightHubTV (via GiveMeSport). Woodley even said Mayweather's team wants him to come to Las Vegas, so he may end up training with him more. Mayweather might be able to provide a unique perspective on the fight, as Jake Paul's brother Logan Paul went the distance (or did he?) with Mayweather back in June.

Amanda Serrano poses with her two belts at press conference for her boxing match with Yamileth Mercado

The Undercard Features A Championship Fight With The Most Decorated Fighter In Women's Boxing History

Before the main event takes place, Showtime PPV is providing a top-notch championship fight between WBC/WBO Featherweight World Champion Amanda “The Real Deal” Serrano and Super Bantamweight World Champion Yamileth Mercado. Serrano, 32, is the most decorated fighter in women’s boxing history with a professional record of 40-1-1 with 30 knockouts. But 23-year-old Mercado has held her title since November 2019 and is riding a six-fight win streak into the August showdown. Mercado's professional record is 18-2, with 5 knockouts.

With Jake Paul Vs. Tyron Woodley airing on Showtime, it's unlikely that the event will be the high-larious spectacle that Triller put on for the YouTuber's contest vs. Ben Askren, which featured Snoop Dogg and other celebrity commentators, live performances including Doja Cat and Justin Bieber, and a slap contest. But as this is the first live sporting event co-produced by Jake Paul’s Most Valuable Promotions, literally nothing would surprise me. Will Tyron "The Chosen One" Woodley in fact be the one to finally sit "The Problem Child" down? Regardless of how you want the fight to go, it should be ridiculously entertaining. Until then, be sure to check out our 2021 Summer TV schedule for what to watch.

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