mma / Columns

The 10 Best Dan Henderson Fights

October 11, 2016 | Posted by Dan Plunkett

Somehow, he almost did it.

I figured Dan Henderson had a chance – anyone with a punch nicknamed “H-bomb” always has a chance – but I certainly didn’t expect the fight we got. Bisping played his game, but got caught up in Henderson’s on two very dangerous occasions. Later, Henderson picked his spot to end strong, but it wasn’t quite enough.

Afterward, Henderson made official what he had been saying all along. It was his last fight, and what a last fight it was. Most mixed martial arts retirements prove temporary, but at 46, after that performance, and given the amount of time he’s openly talked about retiring, it’s more than likely that Saturday was the final chapter in the career of Dan Henderson.

To salute the man of the hour, I spent much of Saturday looking back at Henderson’s best fights and compiled a list of the top 10.

This is not a list of his best moments or wins. Listed are four fights that Henderson lost, and two close calls that could have easily had different outcomes. In that sense, this list is much better representative of Henderson’s career than one of his best wins or moments. He never had a big run on top, he was never the best fighter in his weight class, and he benefitted from controversial judgement calls both in and out of the cage. However, he fought a litany of elite fighters from various weight classes for almost 20 years – his strength of schedule is perhaps the toughest in the sport’s history. He beat many of those fighters, and many of them beat him. All through it, he remained relevant and near the top. To exemplify that, the earliest fight on this list is from a UFC tournament championship match in 1998; the most recent is from a UFC championship match from Saturday.

10. Henderson vs. Shogun Rua – UFC Fight Night

The rematch between Dan Henderson and Shogun Rua promised fireworks, although nobody expected it to match the high bar set by the first match. Of course, it missed that bar significantly, but the fisticuff legends still delivered a memorable fight. This was the first fight where you could really see the years on Henderson. He’d lost three consecutive fights before this – two slow decisions and a fast knockouts – but none signaled his aging quite like this. For a fighter that was never notably quick or matrix-like, he looked awfully slow and was getting hit an awful lot. He did hurt Rua in round one, but Shogun returned fire with a knockdown. The Brazilian continued the assault with a second round knockdown, and it seemed Henderson was only barely hanging on. Then, in the third round, Rua turned into a right hand. Word to the wise: If you’re going to turn into a right hand, make sure it does not belong to Dan Henderson. Mauricio Rua’s nose will attest to you that this is not a good idea.

9. Henderson vs. Michael Bisping – UFC 100

The knockout heard round the world. Months of buildup on The Ultimate Fighter led to this clash, which will forever live on highlight reels. Henderson was able to touch Bisping in the first round, so the Brit had a sense of his power. By midway through the second round, Bisping was finding his range and getting in and out on Henderson. Then, Henderson threw a right hand that started across the pond and landed on Bisping’s chin in Las Vegas. He’d been loading it all fight, and Bisping circled right into it.

8. Henderson vs. Rampage Jackson – UFC 75

For years fans yearned to see the Pride middleweight (205 lbs.) champion fight the UFC light heavyweight champion. When it finally occurred, it wasn’t Randy Couture or Chuck Liddell fighting Wanderlei Silva as many imagined it would be, but rather two fighters most considered Pride fighters duking it out. In September 2007, Quinton Jackson defended his UFC light heavyweight belt against Henderson, who had won Pride’s title earlier that year, on Spike TV. The match was hard-fought and close, with Henderson getting the edge early and Jackson taking over late to win a decision. At the time, it was the second-most watched MMA fight in US history with 5.811 million viewers.

7. Henderson vs. Rogerio Nogueira – Pride Total Elimination 2005

Henderson had twice fought Rogerio’s larger twin brother Rodrigo, first winning a controversial decision and losing by submission the second time. Pride matched Henderson and Rogerio in the first round of their 2005 middleweight tournament, one of the deepest tournaments in MMA history. There were tremendous grappling sequences and vicious punching exchanges, the combined forces of which tired Henderson. Pride’s 10 minute opening stanza played to Nogueira’s advantage, as he submitted a tired Henderson after eight minutes.

6. Henderson vs. Carlos Newton – UFC 17

The UFC 17 middleweight tournament caught Henderson and future UFC champion Carlos Newton at early points in their respective careers. Henderson had fought just twice prior to the show, while Newton’s experience was double that. In the opening round, Henderson eked out a decision over the formidable Allan Goes, while Newton tore through the less notable Bob Gilstrap in 52 seconds. The fresher Newton hurt and knocked down Henderson multiple times in the final, although Henderson countered with strong ground and pound and at one point a series of knees. Even though Newton got the best of the overtime period, two judges sided with Henderson, who won the fight and the tournament. With the win, he earned a shot at UFC champion Frank Shamrock, which never occurred.

5. Henderson vs. Wanderlei Silva – Pride 33

This match made Henderson a double champion and added another layer to his legacy. Whereas Silva controlled the bulk of their first fight six years earlier, the rematch was almost all Henderson. Silva, who was reportedly battling the flu heading into the fight, didn’t look himself and was slower to the punch, but still managed to tag Henderson at points. In the third round, Henderson scored a spinning back fist that put Silva into retreat. In an exchange shortly thereafter, he clipped “The Axe Murderer” with a left hand to make history.

4. Henderson vs. Wanderlei Silva – Pride 12

The rematch is better remembered, but for my money, this is the better fight. This was Wanderlei Silva at his most brutal. Almost every time the fight was standing, Silva hurt Henderson. Henderson dug deep and fought hard – he hurt Silva in the first round and stood toe-to-toe with him in a great exchange early in round two – but spent a lot of time surviving. This wasn’t the first fight in which Henderson was forced to survive, but it’s the best example of his heart.

3. Henderson vs. Fedor Emelianenko – Strikeforce: Fedor vs. Henderson

Fedor Emelianenko reigned on top of the heavyweight world for seven years before successive losses to Fabricio Werdum and Bigfoot Silva. Heading into his match with Henderson – a veritable legends tour match for lack of anything more sensible in their respective divisions – Fedor was the favorite. He showed why early on, hurting Henderson and swarming for the finish. As he reigned down blows from behind Henderson, the American escaped through the back door and took Emelianenko’s back. Typically when you see fighters in that position, the fighter on the back will look to establish position and perhaps attempt to put hooks in. Rather than the traditional route, Henderson threw a right hand from underneath the former heavyweight kingpin. The punch clobbered Emelianenko and put him out flat on the canvas.

2. Henderson vs. Michael Bisping – UFC 204

Call it recency bias, but this fight deserves a high spot on the list. Bisping vs. Henderson II proved more compelling and exciting than it had any right to be. The idea that 46-year-old Dan Henderson, in his last fight no less, would fight closely with the world champion and come close to a finish should be insane. The fight came to fruition by absurd means. Who could have guessed three weeks out from UFC 199 that Chris Weidman would pull out with an injury, Michael Bisping would replace him and beat Luke Rockhold, Henderson would beat Hector Lombard on the same night, and UFC would ignore the impressive shortlist of deserving fighters to give Henderson the title shot? Given that, it would only make sense that the fight itself would be propelled to absurdity in its best possible form. Henderson almost finished Bisping in round one, knocked him down in round two, then after a couple rounds of hanging back, he came on strong in round five. It was a very good fight, a tremendous story, and an almost perfect way for Henderson to end his career.

1. Henderson vs. Shogun Rua – UFC 139

Could it be anything else? Henderson returned to the UFC riding a wave of momentum following knockout wins over Babalu Sobral, Rafael Feijao, and Fedor Emelianenko. He fought Shogun Rua with a title shot hanging in the balance, and neither fighter cared to give an inch to the other. In one of the greatest bouts in MMA history, Henderson and Rua clobbered each other for five rounds. Once again, Henderson faded late and Shogun completely took over in round five, but Hendo’s heart kept him in the fight to win a decision that just as easily could have been a draw.