UFC® 20: BATTLE FOR THE GOLD took place on May 7, 1999 in Birmingham, Alabama. As the fight began, Randleman immediately secured his first takedown. Kevin maintained top control while landing a barrage of punches that broke Rutten’s nose within the first five minutes, momentarily stopping the action for doctors to evaluate his condition. After Bas was deemed able to continue, Randleman immediately took Rutten back to the canvas, trading punches for 10 minutes, until referee John McCarthy halted action so doctors could address the heavy bleeding from Rutten’s nose. 

Rutten would spend the majority this event fighting and throwing punches from his back, which resulted in Bas landing numerous strikes to Randleman’s head. At the end of regulation, with no winner declared, both athletes advanced to fight for three additional three-minute overtime rounds. Randleman seemed to control two of three rounds, but following 21 minutes of action, Rutten was declared the winner via split decision. This split decision loss is still considered one of the most controversial decisions in UFC history.

Rutten would later vacate the title, giving Randleman a chance to compete for the vacant UFC heavyweight title against Pete Williams at UFC 23.  

Randleman had a personal interest in this matchup, as Williams had recently defeated Kevin’s friend, trainer and coach, future UFC Hall of Famer Mark Coleman, one year earlier at UFC® 17: REDEMPTION. Known as The Kick Heard Round the Worldthis fight was later inducted into the UFC Hall of Fame’s Fight Wing in 2016.

UFC®23: ULTIMATE JAPAN 2 took place on November 19, 1999 in Tokyo, Japan. At the beginning of the match, Randleman quickly advanced to the center of the Octagon, hitting Williams with several punches before securing his first takedown at the 10-second mark. Randleman controlled the action during the majority of the first round, until Williams rocked Kevin with a series of punches in the late frame. 

Randleman recovered for the start of the second round, taking Williams down repeatedly and controlling the pace of the action through the remaining four rounds. Kevin’s numerous takedowns proved to be the deciding factor to winning the fight via unanimous decision and becoming the fifth heavyweight champion in UFC history.

Next, Randleman would successfully defend his title by defeating Pedro Rizzo at UFC®26: ULTIMATE FIELD OF DREAMS, which took place on June 9, 2000 in Cedar Rapids, Iowa. With his victory, he became just the second UFC heavyweight champion to make a successful title defense. Kevin took a four-month break before returning to action to face future UFC Hall of Famer Randy Couture on November 17, 2000 as the main event of UFC®28: HIGH STAKESRandleman would lose the title to Couture, then split his last two fights before leaving the organization after defeating former Strikeforce® light heavyweight champion Renato Sobral at UFC®35: THROWDOWN. He would continue to compete at both light heavyweight and heavyweight in other promotions until retiring in 2011.

During his MMA career, Randleman was known for his power and speed, as he recorded nine knockout victories and nine first round stoppages. A world-class wrestler at all levels, he also secured the second-most takedowns (21) during the time frame in which he competed in UFC from 1999-2002 (Tito Ortiz, 29).