Dan Henderson's Best Fights, A Top Five List

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Dan Henderson vs. Renato Sobral
Rings: "King of Kings"
Nippon Budokan in Tokyo, Japan
February 26, 2000

Thirty-two men enter, one man leaves. That was the concept behind the event that Fighting Network Rings (RINGS) assembled in 1999, pitting the best fighters at the time -- from nine different countries -- against one another in a single elimination tournament that took four months to complete. It was a prehistoric period for mixed martial arts (MMA), but several notable fighters such as Antonio Rodrigo Nogueira, Alistair Overeem, Renato Sobral, Renzo Gracie, Maurice Smith, Gilbert Yvel and Dave Menne were all in the running. It was Henderson, however, who somehow emerged victorious in the end. Sure, he was fresh off a middleweight tournament win at UFC 17 months prior, but the decorated Olympic wrestler had no business winning major MMA tournaments. Not just after turning pro two years earlier, anyway. And it's not like he had a cupcake path, either. Henderson had to go through Bakouri Gogitidze, Hiromitsu Kanehara, Yvel, Nogueira and finally "Babalu" in the finals. It was the start of something special.

Dan Henderson vs. Murilo Bustamante
Pride Shockwave 2005
Saitama Super Arena in Saitama, Japan
Dec. 31, 2005

Pride FC had big plans for Murilo Bustamante when it lured the Brazilian jiu-jitsu ace away from Ultimate Fighting Championship (UFC) shortly after he successfully defended his middleweight belt for the first and only time against Matt Lindland in 2003. However, he got off to a rocky start, losing three consecutive fights, including a technical knockout finish at the heavy hands of Henderson. In 2005, he entered the Pride FC Welterweight Grand Prix, stringing together two straight victories and securing a spot in the final opposite Henderson, who literally punched his ticket to the championship fight with two knockout wins in the opening and semifinal rounds. But once again, it was Henderson who would prevail, earning a split decision from the judges and taking home the 185-pound tournament trophy, as well as the division championship. Another Henderson hardware haul.

Dan Henderson vs. Wanderlei Silva
PRIDE 33: "Second Coming"
Thomas & Mack Center in Las Vegas, Nevada
Feb. 24, 2007

For most of his career, Henderson was a two-division fighter, stuck between the 185 and 205 pound weight classes. However, he was much more successful against lighter competition. Losses to Ricardo Arona, Antonio Rodrigo Nogueira and his brother, Antonio Rogerio Nogueira, made it seem pretty clear that Henderson was in over his head in the 205-pound division. He'd start to change that perception, however, when he decisioned Vitor Belfort at Pride 32: "The Real Deal" in 2006. And he'd prove it wrong altogether when he scored an improbable, and devastating, knockout of Wanderlei Silva in their rematch four months later. Earlier in their careers, "The Axe Murderer" registered a unanimous decision win over Henderson. He would go on an epic championship run, successfully defending his middleweight title several times over the next six years. That would come to a crashing end when Henderson separated him from consciousness with a blistering left hand on the button, which came shortly after a highlight-reel spinning backfist that wobbled the Brazilian. It marked the first time ever in MMA competition that a fighter held two major titles at the same time in different divisions. Dan Henderson, setting records at 36.

Dan Henderson vs. Michael Bisping
UFC 100: "Lesnar vs. Mir 2"
Mandalay Bay Events Center in Las Vegas, Nevada2
July 11, 2009

It was the centennial event for Ultimate Fighting Championship (UFC). It was a hallmark in the history of the promotion, which was headlined by its two biggest draws, heavyweight champion Brock Lesnar and 170-pound deity Georges St. Pierre. Henderson was also on the card, taking on the polarizing Michael Bisping, the culmination of their "U.S. vs. U.K." coaching rivalry on the set of The Ultimate Fighter (TUF) 9. "The Count" was a viable and marketable middleweight contender at the time, and if he could defeat Henderson, was likely guaranteed a title shot against division champion Anderson Silva in the near future. Henderson detonated those hopes with a thundering right hook, which he followed up with a flying face forearm smash as Bisping lay supine, stiff as a board, on the canvas. It was the biggest highlight on the UFC's biggest ever show. Henderson stole the show, scoring one of the greatest, career-defining knockouts ever against one of the sport's most reviled personalities ... on the biggest stage possible. Clutch.

Dan Henderson vs. Rafael Cavalcante
Strikeforce: "Feijao vs. Henderson"
Nationwide Arena in Columbus, Ohio
March 5, 2011

After his epic win over Bisping, with his stock at an all-time high, Henderson opted to walkaway from the UFC after the parties failed to agree on the terms of a contract extension. Strikeforce quickly swooped in and signed him to a deal, as well as rewarded him with an instant title shot against middleweight champion Jake Shields. Despite a marked experience and size advantage, Henderson would drop a disappointing five-round unanimous decision ... even though he nearly finished the fight in the first round. He would rebound with a rematch against Sobral in a light heavyweight number one contender eliminator match in his next fight, more than a decade after their first encounter. He would quickly get back in the knockout win column and earn a crack at Rafael Cavalcante's 205-pound belt. It took him three rounds, but Henderson eventually connected with a flurry of powerful punches that led to a technical knockout stoppage. He was once again crowned champion at the ripe age of 40. An accomplishment that seemingly never gets tired, especially when it happens at such an advanced stage of a career. Old man strength prevails once again.

(Note: This list appears in chronological order. Feel free to share your favorite, and not-so-favorite, "Hendo" memories in the comments section below.)

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