Woodley last fought in March when he suffered the first submission loss of his professional MMA career at the hands of Vicente Luque.
The 39-year-old tapped out to a Brabo choke at 3 minutes, 56 seconds of the first round, two years after he lost the UFC title to Kamaru Usman in Las Vegas.
Tyson concedes that Woodley is the more 'experienced' of the two fighters, in a nod to his 16-fight career with the Ultimate Fighting Championship.
However, 'The Baddest Man on the Planet' does not expect him to come out on top against YouTuber-turned-boxer Jake Paul.
Paul (3-0, 3 KOs) is unbeaten in three pro bouts and former undisputed heavyweight titleholder Tyson reckons the controversial 'Problem Child' will be too much to handle for the former UFC welterweight champion.
Tyson, 55, told The Hotboxin' Podcast: "I'm proud of them. Are they gonna fight? He's fighting an experienced fighter. That's so cool.
"I don't know. Paul's a real good striker, and I think people do him a disservice when they go in there and say, 'He's blonde-haired and blue-eyed, he's a white b----', and I think that also builds their courage up and causes them to get knocked out.
"Jake's gonna beat him. Woodley's not a puncher like that, that's why he wants to fight this guy, to get his last payday probably."
Back in June, Jake's brother Logan Paul boldly claimed he could be the first man to defeat Tyson since Kevin McBride in June 2005, despite his lawyer's warnings that 'you don't stand a chance'.
Speaking on his podcast, he said: "My lawyer mentioned it and he was like, 'No, Tyson will rip your head off, you don't stand a chance'.
"I'm like 'bro, I literally just went through all of this, you can't tell me I can't beat Mike Tyson. Bro, he's old, old.'"
Fellow YouTuber KSI has also backed Logan to get the better of Tyson in a blockbuster fight.
He told the 'IMPAULSIVE' podcast: "Bro, with you and Tyson, I think you could beat Tyson.
"I know people are going to be like, 'Oh, what the f---, JJ?' But, bro, you've got to remember that this isn't Tyson who's 18, this is Tyson who's 55.
"He's a legend, that's the thing, but people don't understand that we train like boxers, man, because we're going in there with the world watching.
"Everyone is saying we can't do this, we can't do that, but do you think we're going in there like, 'Oh, we're YouTubers, we should try and just wing it?'
"No way, bro, winging it is kind of what Deji [Olatunji] did, he thought he could get away with doing the bare minimum.
"He thought, 'I'm kind of strong, I've kind of got some technique, I should be able to just do it,' but bro, we go in and we are gladiators.News Now - Sport News