Wanderlei Silva
Combat sport fans recognize Silva as a fiercely competitive fighter who carried an unyielding intensity in his fights. His fights usually played out as a swinging contest to test the primal instinct and resolve of his opponents. The pair locked horns at Pride 33 back in February 2007 with Henderson banking on the strength of a 21-5 record. Both fighters refused to concede an inch of ground from the opening bell. Henderson started out as the aggressor, loading up on his right hand to find Silva’s chin. During a brief exchange, “Hendo” slipped onto his back while launching an attack that allowed enough time for the Brazilian to capitalize and spend some time on top pounding strikes. Each exchange put fans on the edge of their seats while the pair exercised caution with recognition that even a momentary lapse in judgment would cost them the fight. Silva staggered his foe with a powerful punch towards the end of the first frame, but the American managed to survive and make it to the second round. Henderson harked back to his wrestling skills to neutralize his opponent’s offense in the second. Silva was visibly drained from the grappling exchanges in the second and in the third, Henderson caught him with a spinning backfist, and swarmed when he smelt blood. He caught him with a couple of looping shots before punctuating the finish with a vicious left hook and a thundering right hand on a grounded opponent; the final nail in the coffin.
Michael Bisping
Bisping refused to conform to conventional norms of viewing the fight game solely as a sport and accepted it for what is was at face value. His unapologetic demeanor and refusal to play by the rules of deference ignited several rivalries, including one with “Hendo” amongst many others. Bisping and Henderson’s near-decade-long rivalry ended in a 1-1 split spread across two memorable encounters. They first crossed paths on the ninth season of The Ultimate Fighter serving as rival coaches that ignited a feud between the brash, surging contender in Bisping and Henderson, a Hall of Fame-worthy talent. The UK star shifted into overdrive and kicked the mental warfare games up a notch trying to get inside the skin of Henderson. At their UFC 100 encounter, Henderson was counting on his fists to rebut every verbal jab. He did just that, planting one of the most brutal knockouts captured inside the UFC Octagon, courtesy of the patented “Hendo” bomb that put Bipsing out like a light. Their second encounter at UFC 204 marked Bisping’s first defense of his middleweight throne and also the last fight of Henderson’s career. The pair engaged in a back-and-forth war where the American delivered plenty of ear-splitting strikes that left Bisping bloodied and battered. “The Count” endured through all the punishment and scripted an arc of redemption, scoring a unanimous decision win over Henderson simply based on his resilience, mettle, and volume striking.
Mauricio Rua
Henderson’s first encounter with Rua is at the top of the heap of fights you can show to someone uninvolved in MMA fandom to pique their curiosity about the sport. The fight had everyone in attendance and fans watching around the globe on the edge of their seats. UFC head honcho Dana White at that time called their first clash at UFC 139 one of his top three favorite fights of all time. What started as a one-sided beatdown by Henderson turned into an absolute slugfest where each fighter traded leather. The fight had it all, from momentum’s ebb and flow to grappling sequences, and near-fight-ending moments. In the end, the judges scored the bout unanimously in favor of Henderson. But at the end of the day, it didn't really matter who won or lost, and the bout, as fitting, went down in the UFC Hall of Fame 2018-Fight Wing. “Hendo” managed to paint a definitive conclusion during their second meeting, registering a third-round TKO victory on the Brazilian’s home soil.
Vitor Belfort
To encapsulate all of Henderson’s pivotal clashes in a few words would be a daunting task as each bout added layers to his storied legacy. However, one more iconic rivalry that stood the test of time and stands among the episodes that shaped his trajectory as a fighter are his three clashes with Belfort. The pair first locked horns at Pride 32 back in October 2006 where the American sealed the victory via unanimous decision. Their second clash played out under the UFC banner headling the UFC Fight Night 32 card. Belfort claimed vengeance with a spectacular head kick knockout victory in the first round. Two years later, they squared off for the rubber match and it was Belfort who conquered the rivalry with another first-round knockout victory at the sold-out Ginasio do Ibirapuera in Sao Paulo, Brazil.