Dan Henderson's Worst Fights, A Top Five List

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Dan Henderson vs. Antonio Rodrigo Nogueira
Pride 24: "Cold Fury 3"
Marine Messe Fukuoka in Fukuoka, Japan
Dec. 23, 2002

Henderson came into this contest hungry, looking to rebound from a split decision loss at the hands of Ricardo Arona eight months earlier. He had tasted defeat just twice at this point in his career, with the other blemish being a decision loss to Wanderlei Silva in 2000. "Big Nog," however, was on a tear, winning 12 straight fights heading into the bout. In fact, the last time the slick Brazilian jiu-jitsu player tasted defeat was two years earlier thanks to Henderson in the "Rings" 32-man tournament. He was out for revenge. And he'd get it, as well as add an exclamation point, with an armbar submission -- the first time ever that Henderson was forced to tapout. It also marked the first time ever that Henderson dropped back-to-back contest. And it's the only time in his 14-year career that he went an entire year (2002) without winning a fight. Lots of firsts.

Kazuo Misaki vs. Dan Henderson
PRIDE Bushido 12
Nagoya Rainbow Hall in Nagoya, Japan
Aug. 26, 2006

Just four months earlier, Henderson notched a unanimous decision win over Misaki at Pride Bushido 10 in Tokyo. It was his fourth consecutive victory since suffering back-to-back losses to Arona and Nogueira. It was also his first win since winning the Pride FC 2005 Welterweight Grand Prix, as well as the welterweight title, with a decision over Murilo Bustamante in the tournament finals. He was now poised to defend that grand prix crown, drawing Misaki in the quarterfinal round. Instant rematch! Unfortunately, Henderson would go on to lose a decision, getting bounced out of the tournament and failing to duplicate his grand prix glory. Misaki's good luck continued as he went on to win the whole thing despite being eliminated by Paulo Filho in the semifinals. He'd return to beat Denis Kang by split decision when Filho could not continue because of an injury. Some things just aren't meant to be ... for Henderson, anyway.

Dan Henderson vs. Quinton Jackson
UFC 75: "Champion vs. Champion"
The O2 in London, England
Sept. 8, 2007

Henderson was riding high after his sensational knockout win over Wanderlei Silva under the Pride FC banner to claim the middleweight championship. And when Zuffa purchased the Japanese promotion in 2007, it didn't hesitate to book an instant unification bout between Henderson and UFC Light Heavyweight Champion Quinton Jackson. It was a five-round back-and forth war, during which both fighters had their moments. "Rampage," however, apparently had more of them -- at least according to the ringside judges -- who awarded him with a unanimous decision victory, as well as the title of undisputed 205-pound kingpin. To this day Henderson still feels he did enough to win the match, but that likely does little to soothe the sting of defeat.

Dan Henderson vs. Anderson Silva
UFC 82: "Pride of a Champion"
Nationwide Arena in Columbus, Ohio
March 1, 2008

No rest for the wicked. With one failed bid to unite a title behind him, Henderson had a second chance when he took on UFC Middleweight Champion Anderson Silva in his very next appearance. Remember, Henderson was the Pride FC 203- and 185-pound champion when he made his return to the promotion. This time, however, he would have to do it against a man widely regarded as the best pound-for-pound fighter in the sport. "The Spider" seemed unstoppable, winning his first five fights under the UFC banner in impressive fashion. No one had really even tested him inside the Octagon up until that time. But he certainly had never faced anyone with the wrestling pedigree of Henderson. For the first five minutes, it actually appeared that Silva had finally met his match -- Henderson took him down and pounded on him for the better part of the round, clearly winning it. But things would go south real fast midway through the second frame, and it would end with just eight seconds remaining on the clock, when Henderson succumbed to a rear naked choke. Lord only knows what would have happened in the next few rounds had he been able to hang on for just a little while longer.

Dan Henderson vs. Jake Shields
Strikeforce: "Nashville"
Bridgestone Arena in Nashville, Tennessee
April 17, 2010

Coming off a spectacular knockout win over Michael Bisping at UFC 100, Henderson's stock had likely never been higher since his win over Silva in the waning days of Pride FC. He and the UFC were unable to strike a new deal and Henderson bolted into the open arms (and checkbook) of rival promotion, Strikeforce. It had a similar situation brewing with its middleweight champion, Jake Shields, who was nearing the end of his contract and would likely demand top dollar. And it was no secret that the UFC would drive up the sale price to lure Shields into the Octagon. Strikeforce booked Henderson opposite Shields in an instant title fight, hoping that he could handle Shields and ultimately demonstrate his true worth (or lack thereof). On paper, Henderson -- who had competed against the best the sport has to offer at 185 pounds and above -- was no match for Shields, a one-dimensional jiu-jitsu fighter whose true weight class was at 170 pounds. And in the first round Henderson was proving as much, ragdolling the much smaller fighter and nearly finishing him. But Shields would weather the storm and turn the tide in the final four rounds, taking Henderson down, mounting him often and coasting to an improbable unanimous decision victory, as well as a lucrative UFC contract. It all happened much to the satisfaction of UFC President Dana White, who told everyone and anyone that Henderson's best days were behind him. Perhaps that night, but clearly not forever.

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