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YouTuber-turned-boxer Paul resumes his budding boxing career against former UFC welterweight champion Woodley.
Despite being on a four-fight losing skid, the 39-year-old is a considerable step up in competition for 'The Problem Child'.
And MMA star Michael Page believes it may be a bridge too far for the 3-0 fighter.
"Tyron Woodley - if all goes to plan - should just sleep Jake quickly," he told MMA Fighting.
'Venom' added: "[Paul] will feel the difference between somebody that has been in the game a long time. that's experienced in terms of striking, whereas the argument with Ben Askren before, somebody that had not just retired, he checked out a long time ago and his strength was never his standup anyway. I saw it going that way.
"This fight is very different. I see Tyron Woodley going in there and correcting the world, because I feel like there's a crazy shift right now with what's going on.
"But Tyron Woodley is gonna be the guy to correct that."
Woodley himself is confident in stopping Paul too, predicting a third-round knockout victory when he makes his boxing debut.
Speaking to Michael Bisping, he said: "I think three. First round sounds cocky, sounds dope, but I just know that if I'm fighting Tyron Woodley, everyone is going to tell him to cover up, weather the storm, clinch him, grab him, keep him away from you, stay at distance, watch out for the right hand.
"I've got to set a couple traps so I may need a round or two to set some traps, see what he responds to and I think third round I should be able to clean up the deal."
Dear @jakepaul keep the I'm taking your head clean off your neck! #GotchaSoul pic.twitter.com/f7Ba8MELJ4
- Tyron T-Wood Woodley (@TWooodley) June 1, 2021
Paul is coming off a one-round demolition of Ben Askren, while Woodley hasn't fought since his submission defeat to Vicente Luque at UFC 260 last March.
Featured Image Credit: PA/Triller
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