Last Saturday, in the main event of UFC 204, a 46-year-old Dan Henderson fought the final fight of his MMA career. He did so against an old nemesis in Michael Bisping, with the UFC middleweight crown on the line. Despite a spirited effort, Henderson would come up short on the scorecards, failing to win the belt as he did in his two previous UFC title shots.

Though he was never able to win gold in the UFC, Henderson accomplished some incredible feats over the course of his 47-fight career, winning titles in other major promotions, engaging in unforgettable wars, and dishing out some of the most iconic knockouts in MMA history.

Without further ado, here are our five favorite moments of the retired legend’s incredible career (in no particular order).

1. Dan Henderson vs. Wanderlei Silva 2 

Dan Henderson and Wanderlei Silva first met all the way back in the year 2000 under the PRIDE banner. On that night, Silva came out on top with a decision win. Seven years later, the two fighters would meet again in a bout that would go down as the last of Henderson’s long-running Pride career.

This time around, Henderson owned the title in Pride’s 183-pound welterweight division, while Silva was the ruler of Pride’s 205-pound middleweight division. If Henderson won, then, he would become the first fighter ever to simultaneously hold titles in two weight classes in a major organization. And win he did. After finding some early success with his wrestling, the American put his Brazilian foe down with ring-shaking left hand, blasting his way into the MMA history books as he did.

2. Dan Henderson vs. Fedor Emelianenko 

Henderson, who performed best at middleweight and light heavyweight, was famous for his willingness to jump up to heavyweight if the opportunity for a marquee fight presented itself. Given this fact, it came as no surprise when the American happily headed north of 205 pounds when he was offered a super fight with Russian legend Fedor Emelianenko.

Though Henderson very nearly became the latest victim of Emelianenko’s incredible punching power in this fight, he stole the momentum late in the first round, coming out on top in a quick scramble, and shutting the lights out on the legend with a rocket-fuelled ground strike. This incredible performance would mark his last fight under the Strikeforce banner.

3. Dan Henderson vs. Mauricio “Shogun” Rua 1

Henderson’s first bout with Mauricio “Shogun” Rua didn’t end with a knockout, but it deserves a place in the history books all the same. This fight with Shogun, who Henderson had never fought before despite their simultaneous runs in Pride, occurred in 2011. It would go down as one of the most legendary wars in the history of fighting.

For five rounds, the two legends pelted each other with heavy artillery, battering each other to the brink of consciousness and forcing several major momentum swings. And while it’s arguable that the bout should have gone to Shogun – or even been ruled a draw – Henderson ultimately came out on top with a contentious decision win.

A little over a year later, Henderson and Shogun would go at it again, and this time, Henderson would earn a much more emphatic win, braving some early adversity to score a third-round TKO.

4. Dan Henderson vs. Rafael “Feijao” Cavalcante 

Henderson’s first title shot under the Strikeforce banner would occur at middleweight, where he took on an unheralded Jake Shields. Though Henderson very nearly polished his foe off in the first round, he wound up fading later in the fight, and gave up a decision as a result. Henderson’s next Strikeforce title fight occured a little less than a year later, this time at light heavyweight opposite wickedly powerful Brazilian Rafael “Feijao” Cavalcante.

This time around, the American legend made sure not to let the opportunity go to waste. Though he was dropped by Feijao in the first round, Henderson found his opening in the third, levelling his foe with a punch, and polishing him off with a storm of ground-and-pound.

5. Dan Henderson vs. Michael Bisping 1.

You knew this one would be on the list.

Henderson and Bisping first met back in 2009, on the main card of the landmark UFC 100. The bout marked their opportunity to settle the grudge they’d cooked up as opposing coaches on season 9 of The Ultimate Fighter.

Though Bisping would walk away from their 2016 rematch as the victor, Henderson won this first encounter in the most emphatic way possible, removing Bisping’s batteries with a meteor of a right hand. This one-hitter-quitter would go down as one of the most iconic and violent knockouts in MMA history. It would also wind up inspiring Henderson’s official logo.