It was the first-ever fight between Ultimate Fighting Championship Hall of Fame inductees inside the Octagon: Randy Couture met Mark Coleman in the UFC 109 main event on Feb. 6, 2010 at the Mandalay Bay Events Center in Las Vegas, as two MMA pioneers faced off in the modern era.

Couture and Coleman were supposed to lock horns at UFC 17 in 1998 before an injury to the former nixed those plans. Coleman later left for Japan, where he won the 2000 Pride Fighting Championships open weight grand prix. After a loss to Fedor Emelianenko at Pride 32 and a two-year layoff, “The Hammer” returned to the Ultimate Fighting Championship. Coleman made his light heavyweight debut at UFC 93, losing to Mauricio Rua by third-round technical knockout in a “Fight of the Night” performance. A three-round unanimous decision over Stephan Bonnar got Coleman on track in his new weight class and set up his historic clash with Couture.

Fresh off of a controversial decision against Brandon Vera, Couture proved to be the superior fighter when he duked it out with Coleman. He eventually wore down the 1992 Olympian and choked him unconscious in the second round.

There were other notable fights at UFC 109. Chael Sonnen won a decision from Nate Marquardt in a co-main event that netted both men “Fight of the Night” bonuses; Paulo Thiago earned “Submission of the Night” honors following his brabo choke finish on Mike Swick; and Matt Serra was awarded “Knockout of the Night” on the heels of his first-round stoppage against Frank Trigg. The prelims saw four-time NCAA All-American and future Bellator MMA champion Phil Davis sweep the scorecards against Brian Stann with 30-27, 30-26 and 30-26 marks from the judges.

Couture went on to face James Toney in an infamous MMA-versus-boxing spectacle before retiring after a knockout loss to Lyoto Machida at UFC 129. Meanwhile, Coleman never again set foot inside the cage, calling it a career following his encounter with “The Natural.”