Watch Jake Paul vs Woodley Live Stream Online 29 August Boxing (8/29/2021)

Jake Paul looks to build a 4-0 professional boxing record when he takes on former UFC Welterweight champion Tyron Woodley to headline a pay-per-view boxing fight card at Rocket Mortgage Fieldhouse in Cleveland, Ohio on Sunday, August 29 (8/29/2021). Jake Paul vs. Tyron Woodley: How to watch YouTube star face a UFC champion | Time, TV, live stream, PPV price

Jake Paul vs. Tyron Woodey will headline a 5-bout fight card on Showtime pay-per-view, which is available to buy on Showtime and Fite TV.

The main event is expected to be the toughest fight of Paul’s career, as he faces former UFC Welterweight champion and active UFC competitor Tyron Woodley, a.k.a., “The Chosen One.” Woodley defended his title four times before losing it to Kamaru Usman, and has lost four fights straight. Nevertheless, he is a renowned striker, and will provide Jake Paul with the “real” challenge some critics have been calling for.

Still, Paul is the -190 favorite for the 8-round, cruiserweight bout, according to CBS Sports, and an undefeated 3-0 record helps his case. For Woodley (+160), this will be his first foray into professional boxing.

“This will be the biggest pay-pay-view of the year,” Woodley told MMA Junkie. “I said it a long time ago, people thought it was funny. No other fight this year in boxing, in MMA this year has more people wondering what the f*** is going to happen. This is that fight. I’m telling you right now: It’s war.”

The fight card starts at 8:00 p.m. ET on Showtime Pay Per View and Fite TV with the main event walk time expected around 10: p.m., but don’t tune in too late in case the preceding fights go quick.

Elsewhere on the fight card, Amanda Serrano and Yamileth Mercado square off for the unified women’s featherweight title. Serrano has an impressive 40-1-1, and has competed across seven divisions in her career.

Here’s the full fight card for Sunday:

Jake Paul vs. Tyron Woodley, cruiserweight

Amanda Serrano vs. Yamileth Mercado, unified women’s featherweight titles

Daniel Dubois vs. Joe Cusumano, heavyweight

Ivan Baranchyk vs. Montana Love, welterweight

Tommy Fury vs. Anthony Taylor, cruiserweight

In the latest fight of YouTube celebrity Jake Paul’s boxing career, the 24-year-old with a 3-0 record will face the toughest challenger of his career in 39-year-old former UFC welterweight champion Tyron Woodley on Sunday, August 29, 2021 (8/29/21) at Rocket Mortgage FieldHouse in Cleveland, Ohio.

The fight card highlighted by the fight between Paul and Woodley begins around 8 p.m. ET on Sunday, August 29. The event will be broadcast LIVE on Fite.TV. Fans can order the fight on pay-per-view for $59.99 at FITE.TV. Sign up to watch the fight here.


What: Jake Paul vs. Tyron Woodley

When: Sunday, August 29

Time: Fights begin around 8 p.m. ET. Paul vs. Woodley main event should begin around 11:15 p.m. ET, but it depends on length of other fights.

Where: Rocket Mortgage FieldHouse in Cleveland, Ohio


Jake Paul is a (-190) favorite in this fight while Tyron Woodley is a (+160) underdog, according to the latest Caeser Sportsbook odds.

When Jake Paul first began boxing, he said he didn’t think he’d be in the position he’ll hold Sunday night — as the A-side fighter competing on a major Showtime PPV. But so far, Paul has been successful enough (inside and outside of the ring) to earn this spot, and if he can beat former UFC champion Tyron Woodley, the controversial YouTube star will continue to get big-time paydays and receive massive amounts of attention. Here’s everything you need to know about Jake Paul vs. Tyron Woodley, including the odds, their records and a prediction on who will win.

You could dismiss Paul’s first two victories, against fellow YouTuber AnEsonGib and former NBA player Nate Robinson, as less-than-impressive because of the opposition, but Paul’s destruction of Ben Askren, at least a legit MMA star, opened the eyes of many. And Paul is riding that wave of adulation to make himself a PPV headliner in the process.

“There’s no other fighter that’s 3-0 and taking fights against champions,” Paul said this week. “I want challenges, and I want to push myself. I was much more motivated in training camp because I know this is a dangerous opponent. I expect him to come out sharp and I expect this to be a fun one.

“I’m polarizing, I get it. I don’t care what people think. Most people aren’t like that. They’re scared to rub people the wrong way. Some people want to see me lose, but I’m here to stay.”

Like Askren, Woodley is a former MMA standout. Woodley has impressive striking power, at least in the UFC Octagon, and even though he’s making his pro boxing debut, he could be the first to really test Paul’s chin.

“I think in general with combat sports, one person does something and people want to replicate it. This is a real fight though,” Woodley said. If you look at the way we’re built, this is a real fight. Some people took this lightly and that’s why they came up short against him. We’ve been training since before this fight was even signed.”

Clearly, Askren took Paul lightly and got knocked out in the first round because of it. The question is: Even if Woodley is in great shape, will his lack of boxing experience lead to the same result for Paul?

“None of his accomplishments matter on Sunday night,” Paul said. “I’m sending him into retirement and turning him into a meme. People are going to see all of my skills. People are going to be surprised. I haven’t shown anything yet. Here’s more info on the Jake Paul vs. Tyron Woodley showdown that U.S. viewers can watch for $59.99 on Showtime PPV beginning at 8 p.m. ET.