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Two UFC Hall of Famers pushed each other to the limit in the longest MMA fight of all time

On this day in 2000, two of the most legendary fighters in MMA history went further than anyone else.

Royce Gracie was already an iconic figure in the martial arts community by the end of 1994 after he had won the first, second and fourth UFC tournaments.

The legacy of Gracie’s reign at the top of the sport was already defined but he’d still go on to have some highly significant bouts in the years to come.

In 1995, he faced Ken Shamrock in their record-breaking inaugural UFC Superfight Championship clash which remains the longest fight in UFC history at 36 minutes.

The pioneer would soon make his way to Japan where another rival was awaiting him after beating Royce’s brother Royler in November of 1999.

Royce Gracie on stage at the UFC Hall of Fame 2020 Induction Ceremony
Photo by Chris Unger/Zuffa LLC

Royce Gracie and Kazushi Sakuraba fought for an hour and a half before the Japanese star was declared the winner

The eventual meeting between Royce Gracie and Kazushi Sakuraba in the quarter finals of the PRIDE Grand Prix in 2000 was a highly anticipated affair.

With wins over the likes of Royler Gracie and Vitor Belfort, Sakuraba was becoming a big star in Japan but he was going to have to play by the Brazilian’s rules if they were going to face off.

The Gracie family wanted a specialist ruleset for this fight after they specifically entered the tournament for this matchup.

Royce Gracie leads Georges St-Pierre onto the stage at UFC 167 open workouts
Photo by Josh Hedges/Zuffa LLC/Zuffa LLC via Getty Images

An unlimited number of 15-minute rounds, with no referee stoppages, and the only method of victory being knockout, submission or the corner throwing in the towel was their conditions and though these rules did receive some pushback, they were put in place.

Due to the rules regarding time limits and stoppages, the fight doesn’t exactly make for exhilarating viewing but it is a fascinating watch as the Gracie’s plan and custom rules started to backfire on them.

The fight ended up lasting an hour and a half where at that point, it had become a battle of attrition that the Japanese fighter was winning even if neither man was able to knockout or submit their opponent.

Kazushi Sakuraba poses on stage at the UFC 245 Ultimate Media Day
Photo by Jeff Bottari/Zuffa LLC via Getty Images

Not only did he appear to have a superior gas tank, Sakuraba caused significant damage with leg kicks which resulted in a broken femur, meaning that Gracie had very little stability and options.

The towel was eventually thrown in at the end of the sixth round with Sakuraba standing tall after handing Gracie the first loss of his MMA career.

Kazushi Sakuraba cemented himself as ‘The Gracie Hunter’ in 2000

After he submitted Royler Gracie at PRIDE 8 in 1999, Kazushi Sakuraba was referred to as ‘The Gracie Hunter’ which added plenty of heat to his eventual matchup with Royce Gracie.

This reputation would only increase the following year after he outlasted Royce in one of the most historic MMA bouts of all time.

Sakuraba went on to beat two more members of the Gracie family that same year, submitting Renzo Gracie in August and beating Ryan Gracie via decision in December.

Seven years later, Royce would eventually get his revenge when he beat Sakuraba via decision at Dynamite!! USA in June of 2007.

Both men are now in the Pioneer wing of the UFC Hall of Fame.