Looking back at the time Bas Rutten became UFC champion

Long before he was internet famous for being the most in-shape 59-year-old ever to grace a yacht, Bas Rutten was one of the best mixed martial artists on the planet. Excluding a Michael Jordan-esque past his-prime return to the sport, Rutten's career effectively ended after he won the UFC heavyweight championship against the late Kevin Randleman on May 7, 1999 at UFC 20: Battle for the Gold. It was one of the biggest fights of the early era of the promotion.

Despite being the older athlete, Rutten represented the evolution of the sport, an elite kickboxer who had focused for years on his grappling and submissions to become a true mixed martial artist. Rutten had started his career fighting in Japan's Pancrase promotion against some of the sport's biggest names like Ken Shamrock, Frank Shamrock, and Maurice Smith.

Early in his promotional run he was submitted on three separate occasions. This led to Rutten training heavily in grappling as he realized he could not reach the top of the sport with just his striking skills. By the time he left Pancrase, Rutten had used his newly well-rounded skill set to go on a 19 fight unbeaten streak and become a multiple time King of Pancrase.

Bas Rutten won the UFC title at UFC 20 in 1999

In stark contrast to Rutten, Randleman was cut from the same mold as previous UFC heavyweight champions Randy Couture and Mark Coleman, the latter of which was Randleman's coach and mentor. He was a three-time All-American and two-time national champion while wrestling at Ohio State University and his fighting style was built off of that wrestling.

Randleman started his career in Brazil before signing with the UFC to take on Maurice Smith at UFC 19: Ultimate Young Guns. That fight was part of The Road to the Heavyweight Title, a tournament that would crown a new champion, as the previous one, Randy Couture, had vacated his belt due to an ongoing contract dispute with the UFC.

With Randleman's avenging Coleman's loss to Smith and Rutten defeating Tsuyoshi Kohsaka with a last-minute knockout, the matchup was set for the vacant belt. We would have Rutten, who the UFC was billing as the greatest martial artist in the world, taking on arguably the best athlete and collegiate wrestler to transition into mixed martial arts.

Within 30 seconds of regulation time, this fight took place before the existence of the unified rules of mixed martial arts and rounds, Randleman was able to secure the takedown and start battering Rutten with ground and pound.

Just shy of the five-minute mark of the fight, referee John McCarthy stopped the action to check on a cut on the nose of Rutten. Unlike the rules of today, the fight resumed on the feet. Within 30 seconds Rutten threw one of his trademark kicks to the liver which Randleman was able to catch and put Rutten right back on the ground. However, the kick appeared to damage the body of Randleman as his pace noticeably slowed. After another five minutes, McCarthy stood the fighters up again to check on the cuts on Rutten's face.

Watch Bas Rutten vs. Kevin Randleman

During this stoppage, Coleman could be seen in Randleman's corner gesturing to McCarthy to stop the fight as it appeared that Rutten might not be able to continue. Coleman did not get his wish and the fight continued. Randleman took Rutten down again, but this time Rutten was active off of his back, throwing elbows and punches that cut the head of Randleman.

After 15 minutes of fighting and with both fighters able to continue, the fight went to overtime. Randleman was now visibly fatigued and Rutten stalked him around the cage. Randleman once again leaned on his All-American wrestling and was able to secure the takedown but much like the end of regulation time he threw very little offense while Rutten battered him from bottom position. The rest of the first three minute overtime period continued in this fashion

As the second overtime period started, Rutten was able to land some strikes and stuff Randleman's first takedown attempt. Just as it appeared Rutten would be able to remain on his feet and finally utilize his standup skills, Randleman secured one last takedown. The last two minutes of the fight looked very similar to the first 19 with Rutten on his back defending the ground and pound from Randleman while trying to find spots of his own to throw short punches and elbows.

At the time, UFC fights were not scored and the three judges simply decided who they thought won the fight as a whole. With Rutten's face bloodied, his nose broken and Randleman looking relatively healthy save for a couple of cuts on the top of his head, the judges rendered their decision. In a result so controversial that the judging criteria would soon be changed, Rutten was declared the winner due to him being viewed as the more effective striker.

The careers of Rutten and Randleman took very different paths after their fight. Rutten vacated the belt before ever defending it as he attempted to move down a weight class and become the first UFC fighter to win championships in two weight classes. Unfortunately, injuries caught up with him and he never fought in the UFC again. Randleman returned to the Octagon later that same year and avenged another one of Coleman's losses, defeating Pete Williams and becoming the UFC heavyweight champion.

Both men are now enshrined in the UFC Hall of Fame, their contributions to the sport forever remembered. Rutten helped to lay the foundation for today's well-rounded mixed martial artists and Randleman continued the legacy of elite collegiate wrestlers winning at the highest levels of the sport.