Kevin Holland gives brutally honest prediction for potential Mike Perry vs. Tyron Woodley boxing match: "We all know who we'd have our money on"

Kevin Holland has given a seemingly definitive prediction for a potential Mike Perry vs. Tyron Woodley fight. 'Trailblazer' opined that though he foresees a clear favorite, the matchup would be entertaining.

Holland has extensively competed in the UFC welterweight and middleweight divisions. He's 2-3 in his past five octagon appearances and is coming off a first-round TKO defeat against Roman Dolidze at UFC 307 in October 2024.

Former UFC welterweight champion Woodley departed the UFC in 2021, on a four-fight losing streak. 'T-Wood' later competed in professional boxing, losing twice to YouTuber-cum-boxer Jake Paul.

Ex-UFC welterweight contender Perry exited the UFC in 2021, on a two-fight losing streak. 'Platinum' then competed in a Triad Combat match and in bare-knuckle boxing bouts in the BKFC. He's coming off a TKO loss in a professional boxing match against Jake Paul in July 2024.

On his Overdogs Podcast, Mike Perry recently alluded to his cordial relationship with Tyron Woodley. Perry recalled directing trash talk against Woodley before eventually meeting him at a seminar and burying the hatchet.

Perry recently launched his Dirty Boxing Championship, an organization that features hybrid-rules striking-centric boxing matches. He speculated about how a potential fight between himself and Woodley would play out under those rules:

"Maybe me and 'T-Wood' go in Dirty Boxing."

Podcast guest Kevin Holland chimed in by stating:

"That'd actually be pretty good. That'd be a -- it'd be a scrap. You know? We all know who we'd have our money on. But it'd be a scrap."

Perry responded by indicating that Woodley was knocked out cold by Jake Paul in their rematch, whereas he (Perry) got back up after multiple knockdowns before ultimately getting stopped via TKO by the YouTuber. 'Platinum' said:

"I got up every time Jake Paul knocked me down."

Kevin Holland then clarified that he was picking Perry to beat Woodley:

"I had my money on you. I don't think Woodley could hang."

Mike Perry replied by suggesting he thought Holland was picking Woodley to beat him in the potential fight. Holland responded:

"I think you and Woodley would be -- it'd be entertaining for sure. I mean, people would pay for it. I mean, we know who would win. But people would pay for it."

Watch Holland and Perry discuss the topic below:

Watch the podcast episode below (*comments at 1:11:28):

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Kevin Holland on Tyron Woodley being stopped by Jake Paul

Kevin Holland fights former ONE middleweight and light heavyweight champion Reinier de Ridder in a middleweight bout at UFC 311 (Jan. 18, 2025). Meanwhile, Mike Perry has been lobbying for a fight, possibly in the BKFC. Moreover, in 2024, Tyron Woodley signed with the GFL (Global Fight League), a new MMA promotion that'll be launched in 2025.

The December 2024 podcast conversation with Perry wasn't the only time Kevin Holland picked against Tyron Woodley. As reported by TheMacLife in June 2021, Holland disapproved of Woodley being the MMA community's supposed representative to box against Jake Paul.

Woodley subsequently lost to Paul via split decision in August 2021. 'T-Wood' was then knocked out in their rematch that December. Holland later tweeted about Woodley possibly having to fall back on his hip-hop career, implying that the loss hurt his fighting career:

"Back to rapping Twood go. Dang man."