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From the Ring to the Cage: When Boxers Stepped into MMA

Writer's picture: Austin JonesAustin Jones

James Toney vs Randy Couture
James Toney vs Randy Couture

Boxing and mixed martial arts (MMA) may share combat at their core, but the differences in skill sets make transitioning between the two sports a monumental challenge. Over the years, a handful of professional boxers have ventured into the MMA cage, with varying degrees of success. Let’s take a look at some notable instances when boxers tried their hand at MMA.


James Toney

  • Event: UFC 118 (2010)

  • Opponent: Randy Couture

  • Result: Loss via submission (arm-triangle choke) in the 1st round.

James Toney, a multiple-division boxing champion, made headlines when he stepped into the Octagon against UFC legend Randy Couture. The fight was a one-sided affair, with Couture quickly exploiting Toney’s lack of grappling skills, showcasing the challenges boxers face in adapting to MMA.


Art Jimmerson

  • Event: UFC 1 (1993)

  • Opponent: Royce Gracie

  • Result: Loss via submission (mounted strikes) in the 1st round.

Art Jimmerson’s foray into MMA is infamous for his decision to wear one boxing glove during the fight. Royce Gracie’s ground game overwhelmed Jimmerson, who tapped out before taking significant damage, marking an iconic moment in MMA history.


Holly Holm

  • Transition Success: Former professional boxer turned MMA fighter.

  • Achievements in Boxing: Multiple-time world champion in three weight classes.

  • MMA Highlights: Became UFC Bantamweight Champion after defeating Ronda Rousey at UFC 193.

Unlike many boxers who struggled in MMA, Holly Holm made a seamless transition, becoming a dominant force in both sports. Her head-kick knockout of Ronda Rousey remains one of the most memorable moments in MMA history.


Claressa Shields

  • Event: PFL 4 (2021)

  • Opponent: Brittney Elkin

  • Result: Win via TKO (punches) in the 3rd round.

  • Event: PFL 8 (2021)

  • Opponent: Abigail Montes

  • Result: Loss via split decision.

The two-time Olympic gold medalist and undisputed boxing champion ventured into MMA with high expectations. While Shields demonstrated potential, particularly in striking, grappling proved to be her Achilles’ heel.


Ray Mercer

  • Event: Adrenaline MMA 3 (2009)

  • Opponent: Tim Sylvia

  • Result: Win via KO (punch) in the 1st round.

Ray Mercer’s transition to MMA culminated in a shocking 9-second knockout of former UFC heavyweight champion Tim Sylvia. The bout showcased the devastating power boxers can bring to the cage, even with minimal MMA experience.


Ricardo Mayorga

  • Event: Omega MMA 9 (2013)

  • Opponent: Wesley Tiffer

  • Result: No contest (illegal knee).

Known for his brash personality in boxing, Ricardo Mayorga’s MMA career was short-lived and marred by controversy. Despite his aggressive style, he struggled to adapt to the multifaceted nature of MMA.


Heather Hardy

  • Transition Success: Balanced careers in boxing and MMA under Bellator.

  • Debut: Bellator 180 (2017)

  • Opponent: Alice Yauger

  • Result: Win via TKO (doctor stoppage) in the 3rd round.

Heather Hardy successfully transitioned into MMA, leveraging her striking skills while adapting to the sport’s complexities. Her determination allowed her to achieve moderate success in both disciplines.


Francisco "Paco" Bueno

  • Background: Former boxer who competed in PRIDE Fighting Championships.

  • Result: Faced significant challenges, often losing to skilled grapplers.

Bueno’s transition highlights the steep learning curve boxers face when stepping into a sport that demands proficiency in grappling and striking.


Dada 5000 (Dhafir Harris)

  • Background: Known more for backyard brawling with boxing experience.

  • Event: Bellator 149 (2016)

  • Opponent: Kimbo Slice

  • Result: Loss via TKO due to exhaustion.

Dada 5000’s bout with Kimbo Slice was less a technical display and more of a spectacle. His limited MMA skills were evident, and the fight ended dramatically due to exhaustion.


Fight.TV Breaks Down Boxers & MMA

Boxers entering the MMA cage face a monumental task of adapting to the diverse skill sets required. While some, like Holly Holm, found tremendous success, others struggled to bridge the gap. These crossovers continue to capture the imagination of fight fans, serving as a testament to the challenges and excitement of blending two combat sports.


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