Ranking every Jake Paul boxing win so far

3. Tyron Woodley I – Aug. 21, 2021

The first of the two bouts with former UFC welterweight champion Tyron Woodley was fought in Paul’s hometown of Cleveland. Heading into the match with Paul, Woodley suffered four straight defeats in the UFC and would be making his professional boxing debut. Much like, Askren Woodley wasn’t particularly known for his striking as an NCAA Division I collegiate wrestler. But, he was viewed as another step up in competition for the then 24-year-old Paul.

Woodley did test Paul as, at one point, he did hurt the younger social media star sending him into the ropes. Still, for the majority of the fight, the former UFC champion had his offense on layaway, allowing rounds to slip by him one after the other.

After eight rounds, Paul was awarded a split decision victory with scores of 77-75 and 78-74, with one judge scoring the fight 77-75 for Woodley. In some respects, both men underperformed; however, Paul did show grit and proved that he would not wilt at the first sign of adversity.

2. Tyron Woodley II – Dec. 18, 2021

Woodley’s showing in the first encounter with Paul left many wondering if he could have won if he had just applied more pressure and thrown more punches. The rematch between Paul and Woodley took place in Tampa, FL, at the Amalie Arena, and this time Paul would leave no doubt.

Initially, Paul was set to take on Tommy Fury; however, the younger brother of Tyson Fury pulled out due to medical issues leaving room for Woodley to step in for a second bout.

However, the then 39-year-old Woodley failed to improve upon his performance in his first fight with Paul. The match was fought at a slow pace with five uneventful rounds, then in the sixth, a sweeping right-hand from Paul sent Woodley crashing down in brutal fashion face-first to the canvas. The fight was immediately called off. The knockout won knockout of the year from ESPN and streaming service DAZN.