Jake Paul expects to go deeper in his next fight than he has any at point thus far in his young pro career.

Though not by much.

The brash YouTube star-turned-developing cruiserweight will enter his fourth sanctioned bout, once again taking on an opponent making their pro debut. The latest to step to Paul is former UFC welterweight champion Tyron Woodley, with their fight to headline a Showtime Pay-Per-View event August 29 at Rocket Mortgage Fieldhouse, home of the NBA’s Cleveland Cavaliers.

Despite having never before fought in sanctioned pro bout, Woodley was best known for his pure punching power and an effective striker during his peak years in mixed martial arts. In that regard, it’s an upgrade from the trio of overmatched foes who have faced Paul to this point.

“I love it. I haven’t been hit in three fights,” Paul noted during a press conference held Tuesday in Los Angeles to formally announce the event. “That’s a fact. I haven’t been hit in the face. As a professional boxer, that’s sort of unheard of."

Paul (3-0, 3KOs) has fought a total of less than nine minutes worth of ring time since turning pro last January. The only opponent to see round two was former NBA star Nate Robinson, who was flattened in the 2nd round of their November 2020 clash as the chief support to a Triller PPV event headlined by the high-profile exhibition between Mike Tyson and Roy Jones Jr.

In his most recent start, Paul needed just 119 seconds to turn away former Bellator champion Ben Askren, who was best known for his wrestling skills as a mixed martial artist. It is a shared area of expertise for Woodley, who was in Askren’s corner that night and made a point to call out Paul immediately thereafter. The wish was granted and now comes complete with a vow to inflict pain upon the current cruiserweight prospect.

“Your ass gonna get hit in this one,” vowed Woodley.

Paul not only doesn’t doubt it, but is actually banking on it to happen.

“Tyron Woodley is a perfect person to maybe get me to the third round for the first time ever,” notes Paul. "I just want to add some experience under my belt."

Jake Donovan is a senior writer for BoxingScene.com. Twitter: @JakeNDaBox