MMA Top Lists

Mixing the arts: The top ten strange MMA vs. boxing super-fights that already happened

MMA and boxing are together, bound roommates in the same subsection of sports entertainment interests. At some point, maybe 100 or 200 years from now MMA and boxing will have died side by side due to societal pressures or melted into a singular combat sport.

Before our beloved sport is dead on the pavement or boxing and MMA form some shoot-box hybrid league, UFC champion Conor McGregor must face 49-0 boxer Floyd Mayweather on August 26th in Las Vegas. The newest “fight of the century” is not the first time a MMA fighter has traded strikes with a professional boxer but it is perhaps the only time when the label of super-fight has weighted meaning.

When the bell of round one echoes inside the T-Mobile Arena in Las Vegas and MMA’s Conor McGregor prepares to box Floyd Mayweather, remember the great (and not so great) MMA vs. Boxing scraps of the past 54 years.

Here are MiddleEasy.com’s top ten strange MMA vs. boxing super-fights that already happened

10) WBO NABO Cruiserweight Champion Yosuke Nishijima VS. K-1 Grand Prix Champion Mark Hunt

On Pride FC’s deathbed, they gave MMA fans the odd visual of full-time kickboxer, part-time mixed martial artist Mark Hunt beating the brakes off boxer Yosuke Nishijima. After losing his debut to Hunt, the Japanese boxing champion would go on to lose his final four MMA crossover fights, each more violently devastating than the last.


Mark Hunt vs. Yosuke Nishijima by emrah-bir

9) Light Heavyweight Contender Art Jimmerson VS. Three-Time UFC Tournament Winner Royce Gracie

The boxer versus jiu-jitsu NHB fight under the smoked filled UFC 1 lights that would kick off a generation of MMA talking points. Art Jimmerson and his dumb ass one-glove offense getting completely lost in the ground-fighting maze of Royce Gracie.

8) WBC Welterweight Champion Ricardo Mayorga VS. Street Fighter Level Martinez

Bless your crazy ass heart Ricardo Mayorga. Despite the Fight Gods (and Don King) denying us the visual of Din Thomas ground n’ pounding Mayorga into submission, years later we were able to see the boxer subbed by converted Miami street fighter Level Martinez.


Ricardo Mayorga vs Level Martinez by marley1986

7) Catch Wrestler Kazushi Sakuraba VS. Heavyweight Boxer Rubin Williams

One of JMMA legend Kazushi Sakuraba’s final wins came versus ten-year boxing vet Rubin Williams. In the name of catch wrestling, pro wrestling and MMA, Sakuraba dominates Williams in his one and only MMA fight.


Kazushi Sakuraba vs Rubin Williams DREAM 11 by chuteboxe57

6) WBA, WBC, The Ring Heavyweight Champion Muhammad Ali VS. Wrestler Antonio Inoki

Work, shoot, whatever it was Muhammad Ali versus Antonio Inoki in 1976 personifies fans carnal urges towards freak shows as well as super-fights. The most famous sports figure of the 20th century in Muhammad Ali standing in the same ring as pro wrestling legend Antonio Inoki. What could have been if Ali vs. Inoki was contested under Pride FC rules.

5) WBO Heavyweight Champion Ray Mercer VS. UFC Heavyweight Champion Tim Sylvia

Nine seconds. Nine seconds? Nine seconds! Finally, a gentleman’s agreement for a MMA fighter to stand and trade punches with a professional boxer wearing four ounces gloves. Sorry, Tim Sylvia.

4) Brazilian Jiu Jitsu Black Belt Genki Sudo VS. IBA Super Heavyweight Champion Butterbean

165 pound soaking weight Genki Sudo fighting 300-pound Toughman contest Hall of Famer Butterbean at K-1 Dynamite 2003 is almost too JMMA to handle. We are all one.

3) YouTube Street MMA Legend Kimbo Slice VS. WBO Heavyweight Champion Ray Mercer

Rest in Peace Kimbo Slice’s gentle soul. What happens when you book an Internet Street Fighter against a respected boxing champion? You put them in a cage and have them compete in MMA. Of course, the original streets versus sweet science match-up would end via submission. Makes sense.

2) Boxing Three-Weight World Champion James Toney VS. UFC Heavyweight Champion Randy Couture

Sometimes the most obvious outcomes are the most satisfying. The UFC set-up boxer James Toney to fail and his one-sided ass kicking at the hands of Randy Couture taught fans from either sports nothing. Seeing a multi-disciplined fighter destroy a singled skilled fighter pokes at MMA fan’s deep seeded need to validate their sport as legitimate and at the end of day the mixed martial arts community was content with the blowout “W”.

1) Judo Black Belt Gene LeBell VS. Boxing Middleweight Contender Milo Savage

Gene LeBell Da God. When LeBell crushed on boxer’s Milo Savage throat with a chokehold, nobody knew it at the time, but modern day MMA was birthed.

BLACK BELT: You won in the fourth round, right?

Gene LeBell: Yes. When I choked him out, the ref, who was also the doctor, didn’t know how to resuscitate him with katsu. After he’d been out for 20 minutes, my coach went in and revived the guy. The next morning, the newspaper headlines said, “The Savage Was Tamed.”

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Tommy Messano is a writer residing in Gilbert, Arizona who is best known for his work as a Mixed Martial Arts journalist. His work has been featured on a number of publications, including Sherdog.com, MiddleEasy.com, ESPN.com, the abandoned WCL.com as well as his own site, ULTMMA.com (R.I.P). An Arizona State University alum he can often be found marketing and public relating things to people when not writing on The Internet.