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However, despite those defeats, Woodley will almost certainly be a step up again for Paul as he continues his unorthodox foray into the world of boxing.
After eight years of consistent showings for the UFC, Woodley certainly departs with a Hall of Fame-worthy resume.
Does Paul stand a chance against the seasoned UFC veteran, or will the former MMA star come out on top? Here's what we know about Woodley so far.
Tyron Woodley has spent an illustrious career inside UFC's octagon, fighting some of the best MMA fighters on the planet.
He boasts an impressive 19-7-1 professional MMA record and a 9-7-1 UFC record - and that record would have made for a much better reading had it not been for his four successive losses in his last four fights.
Woodley faced welterweight champion Robbie Lawler on July 30, 2016, in the main event at UFC 201.
That fight ended with Woodley winning the fight via an emphatic knockout halfway through the first round to claim the UFC Welterweight Championship.
Since claiming the title, he defended it successfully four times before his fifth defence against Usman - 'The Nigerian Nightmare' - on March 2, 2019, in the co-main event at UFC 235.
Woodley was put on the back foot for the entire fight and, eventually, lost by unanimous decision - ending his nearly three-year year reign as welterweight champion.
As per reports from Celebrity Net Worth, Woodley is worth an estimated $4m.
On May 31, 2021, news surfaced that Woodley is expected to make his professional boxing debut against Jake Paul this summer.
Paul confirming its date on social media on Tuesday afternoon, as confirmed by The Athletic last month, that he will be fighting Tyron Woodley on Saturday, 28 August.
A date and location for the fight will also be announced at that time.
The proposed showdown between Paul and Woodley is set to headline a major fight card on Showtime.
Woodley hasn't fought since his submission defeat to Vicente Luque at UFC 260 back in March.
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