4 UFC Fighters with Failed Transitions Into Boxing

While a crossover in skills and abilities employed within both forms of fighting, mixed martial arts and boxing bouts are drastically different. Despite this, some UFC fighters have tested the waters in the ring, albeit to varying degrees of success.

For every Kimbo Slice or Holly Holm success story, there lie plenty of other fighters who haven’t done so well when swapping out grappling gloves for boxing gloves. Whether it be chasing a massive payday or simply due to chasing another passion, here are four UFC fighters whose transitions into boxing didn’t go so smoothly.

1. Tyron Woodley

As the inspiration behind this list, Tyron Woodley’s fight career in the ring features losing two bouts to social media megastar turned boxer Jake Paul. Considered to be one of the greatest welterweights of all time during his prime, Woodley also sported a gifted striking game, which meant his chances in the ring should have boded well.

Rumored to have taken home roughly $ 5 million during his MMA career, a reported purse of $ 2 million for the Paul fight was probably too good to pass up for the former Mizzou All-American. Thinking he’d earn an easy payday against a YouTuber, he’d end up losing the first fight by split decision on August 21, 2021. He would be knocked out – in quite spectacular fashion – in the sixth round of the ensuing rematch.

2. Tito Ortiz

One of the UFC’s first great fighters, the former Light Heavyweight Champion, would finish his career as a Hall of Famer. However, Tito Ortiz seemed to suffer from “Brett Favre Syndrome” – of not knowing when to call it quits. Retiring and unretiring a grand total of three times throughout his career, his reputation would end up going in smoke due to fighting past his prime and messy personal life.

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Nonetheless, wanting to try out boxing, he suited up for Triller Fight Club on September 11, 2021, in a bout versus fellow UFC great Anderson Silva. The “The Huntington Beach Bad Boy” would go on to be dominated by the Brazilian and knocked out cold within the first eighty-one seconds of the match.

3. Ben Askren

Known for his “funky wrestling” style, Ben Askren made a name for himself in Bellator before moving up to the big leagues in the UFC. After suffering the fastest knockout in the promotion’s history thanks to Jorge Masvidal’s flying left knee, he would promptly retire from mixed martial arts fighting shortly thereafter.

In hindsight, knowing the trash-talking aficionado didn’t have the greatest striking game, Jake Paul’s decision to pick Askren as the opponent for his first professional boxing match makes complete sense. Despite the internet thinking the Youtuber did not stand a chance, Askren would go on to be knocked out in less than two minutes by the Ohio native.

4. Mark Hunt

One of the sport’s most powerful hitters, Mark Hunt, possessed a dangerous left hook that would mark his stint in the UFC. He would defeat some of the promotion’s biggest names from 2010 to 2018 but would end up getting released from his contract following a three-match skid during his last year.

Still wanting to compete with other fighting organizations, the New Zealander would go back to his roots and enter the ring one last time versus former rugby star Paul Gallen in December 2020. In an admirable effort, Hunt would end up losing via a controversial decision.

Closing Thoughts

While it’s good to try out new things in life, sometimes it’s best to stick to what you’re good at; unfortunately, these former UFC fighters learned this lesson the hard way. The ring truly isn’t for everyone.

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