The 25 Greatest Legend vs. Legend Fights in MMA History

One day, the Mixed Martial Arts Hall of Fame will have a special wing for its Golden Age, filled with old-fashioned still photographs and two-dimensional footage of the sport's long-gone pioneers.

Consider yourself lucky that you were there to see it in person.

The sport's first great wave of legends is still alive and, for the most part, still kicking. Sometimes literally. And when these legends happen to face one another--as will be the case when Dan Henderson faces Fedor Emelianenko July 30--it's an opportunity not to be missed.

Here's a list of the 25 best examples of legend-on-legend crime.

The challenge was finding the sweet spot in the career arc of the combatants. They couldn't be so old that their meeting was more comedy than drama, but they had to be established enough that their status as legends—or at least great fighters—was secure at the time of the fight, which of course is part of what gives the legend vs. legend fight its luster.

You can be the judge of how well I did. Happy to hear feedback in the comments section. Thanks for reading.

25. Hayato Sakurai vs. Takanori Gomi

December 31, 2005
Pride Shockwave 2005

These two Japanese legends had 51 wins between them when they met in the finals of the 2005 Pride Lightweight Grand Prix.  After an action-packed first round that saw several heavy striking exchanges, The Fireball Kid took the fight to the mat, where he outclassed Sakurai en route to a powerful knockout about four minutes into the round.

The win made Gomi Pride's first lightweight champion and cemented his status as perhaps the best lightweight on planet Earth.

24. Mark Coleman vs Igor Vovchanchyn

May 1, 2000
Pride Grand Prix 2000 Finals

The pioneer of ground and pound and the pioneer of modern-day MMA striking met in 2000 for the Grand Prix title. Coleman bested the Ukranian when Igor tapped under the duress of a nasty barrage of knees to the top of his head.

23. Quinton Jackson vs. Dan Henderson

September 8, 2007
UFC 75

After Pride rode into the sunset (or was put out to pasture…pick your image), these two legends fought to unify the Pride and UFC light heavyweight titles. Jackson, fresh off winning the UFC belt from Chuck Liddell a few months earlier, did just enough in the five-round battle to unify the championship in the UFC’s favor.

22. Wanderlei Silva vs Kazushi Sakuraba II

November 3, 2001
Pride 17: Championship Chaos

Silva had beaten down the great Sakuraba just six months earlier. This time, he did it for the Pride Middleweight Championship, a title he was the first to earn and one he would defend for six year. Six freaking years!

21. Dan Henderson vs. Wanderlei Silva II

February 24, 2007
Pride 33: The Second Coming

Silva had defended Pride’s middleweight belt four times over six years when, in the third round of this rematch, Henderson landed a massive left hook that ended Silva’s night and his title reign.

20. Rich Franklin vs. Anderson Silva I

October 14, 2006
UFC 64

It’s possible, even understandable, that Franklin’s star as a middleweight champion is dimmed rather substantially by the supernova that was his successor.

But Ace entered UFC 64 having defended the belt on two occasions, a fact that made Silva’s first-round knockout win all the more remarkable.

To the surprise of no one, I couldn't find full fight footage, but the video contained herein has some of the highlights from the contest (and is a pretty darn good Silva highlight reel to boot).

19. Wanderlei Silva vs. Mirko “Cro Cop” Filipovic II

September 10, 2006
Pride Final Conflict Absolute

The two fought to a draw in their first meeting, one in which the rules stipulated that going the distance would mean a tie.

 That tie was thoroughly broken by a head kick from Cro Cop in this return engagement.

18. Anderson Silva vs. Dan Henderson

March 1, 2008
UFC 82

This fight, to unify the Pride and UFC middleweight titles, made Henderson 0-2 in unification bouts, as the normally unsubmittable Henderson succumbed to a constrictoresque rear naked choke after an extremely hard-fought battle.

17. Bas Rutten vs Frank Shamrock III

May 16, 1996
Pancrase: Truth 5

These two trailblazers held their rubber match when most other fighters and promotions were just getting started. Rutten got the better of Shamrock after opening a cut that led to a stoppage.

16. Georges St-Pierre vs BJ Penn II

January 31, 2009
UFC 94

Penn did plenty of gum-flapping in the run-up to this one, throwing every piece of psyops in his arsenal at the welterweight champ, in hopes that something would lodge in GSP’s purportedly mushy brain.

Nothing did. After four rounds of ground and pound, it was clear to all who the better fighter was. It was even clear to Penn’s corner, who mercifully called for the stoppage.

15. Dan Henderson vs. Wanderlei Silva I

December 9, 2000
Pride 12: Cold Fury

Back when pterodactyls filled the skies and automobiles still started by hand crank, a young MMA promotion called Pride staged a fight between two of the brightest new names in the sport.

Fresh off his UFC 17 middleweight tournament win, the undefeated Henderson was looking to make a name for himself in Japan.

Silva had other plans. Though Hendo swelled Silva’s eye shut with one of his trademark rights, Silva stayed in the match and slugged it out with the Olympic wrestler for 20 minutes, employing nasty punches and stomps to outstrike Henderson and capture the unanimous decision victory.

14. Chuck Liddell vs. Tito Ortiz I

April 2, 2004
UFC 47

Liddell drops Ortiz not one minute into the second round, ending the first chapter in one of the sport’s great grudges with about 19 exclamation points.

13. Quinton "Rampage" Jackson vs. Chuck Liddell I

November 9, 2003
Pride Final Conflict 2003

Sometimes, another guy just has your number. That seems to be the case in the story of Chuck Liddell and Quinton Jackson.

Most UFC fans will remember Jackson’s quick-and-dirty KO of Liddell in the Octagon. But their first fight lasted slightly longer, even if the result was not wildly different. In their first meeting, Jackson punished Liddell and forced a corner stoppage in the second round to gain the TKO.

12. Ken Shamrock vs. Tito Ortiz

November 22, 2002
UFC 40

A seminal fight that saw Ortiz defend his light heavyweight title for a fifth time.

Shamrock’s corner threw in the towel after Ortiz controlled and punished him for three rounds. It also helped start an angry, if lopsided, feud between the two Hall of Famers. Not excessively competitive in the cage, but it did provide plenty of rocket fuel for the hype machine.

11. Matt Hughes vs. BJ Penn I

January 31, 2004
UFC 46

At the time, Matt Hughes was busy carving his name into the UFC’s welterweight strap, which he had successfully defended five times. It had been quite a while since he’d felt a challenge from any welterweight, much less an upstart 155er.

That, as they say, is why they play the games. Penn submitted Hughes in the first round to win the title, and a champion—and a rivalry—were born.

10. Dan Severn vs. Mark Coleman

February 7, 1997
UFC 12

Severn was 14-2 and a two-time UFC tournament winner. Coleman was 5-0 and a two-time defending tournament champion.

Pretty safe to say these were the two clear choices to duke it out for the inaugural UFC heavyweight championship. The smaller Coleman defeated the older Severn via first-round chokeout.

9. Chuck Liddell vs. Tito Ortiz II

December 30, 2006
UFC 66

This one lasted longer than the first, but the result was the same. Ortiz stayed competitive, but in the end, he found himself once again turtled up on the ground at Liddell’s feet, another victim of one of the greatest strikers in MMA history.

8. Chuck Liddell vs. Wanderlei Silva

December 29, 2007
UFC 79

Given that this whole list is basically the Wandy-Liddell show, it makes sense that their collision should be highly ranked.

This one loses points for taking place after the two legends were significantly past their primes, but it still makes the list for living up to every bit of its hype as a strikefest in which both men gave—and absorbed—a great deal of punishment. Liddell eventually won the fight by unanimous decision.

7. Georges St-Pierre vs. Matt Hughes II

November 18, 2006
UFC 65

With one head kick, a torch was passed. GSP finally got over the hump—and exorcised a few psychological demons—when he knocked out Hughes in the second round to win the welterweight title and even his record against the longtime kingpin at 170.

6. Fedor Emelianenko vs. Antonio Rodrigo Nogueira III

December 31, 2004
Pride Shockwave 2004

The epic rubber match that saw Fedor thwart (once again) Big Nog’s quest to regain the heavyweight gold and win Pride’s 2004 heavyweight grand prix.

5. Quinton “Rampage” Jackson vs. Wanderlei Silva II

October 31, 2004
Pride 28: High Octane

Rampage made no secret of the fact that, despite losing to Silva in their first engagement in 2003, he believed himself to be the better fighter. To prove the point, Jackson repeatedly requested a rematch with The Axe Murderer.

#becarefulwhatyouwishfor

Jackson pressed the action and held the advantage for the first round and change, bullying Silva with his wrestling and scoring a knockdown on the Brazilian. But it all came to a halt when a perfectly placed right hook put Jackson on roller skates. One firestorm of knees later, and Rampage was lying unconscious on the ring ropes.

Silva had won the rematch, defended his title (again) and helped put on a fight many called 2004’s finest.

4. Chuck Liddell vs. Randy Couture II

April 16, 2005
UFC 52

One of the most highly anticipated fights in MMA history shattered pay-per-view records and demanded a rubber match.

The fight followed the inaugural season of "The Ultimate Fighter," in which both men were coaches. After months of buildup, the fight lasted barely two minutes, with Liddell scoring his trademark battering-ram TKO on The Natural to even their head-to-head scorecard at one win apiece.

You can watch the fight here.

3. Fedor Emelianenko vs. Mirko “Cro Cop” Filipovic

August 28, 2005
Pride Final Conflict 2005

Two great legends doing what they do best.

Cro Cop gashed Fedor with his inimitable kickboxing, but Emelianenko found a way to survive and outwrestle Filipovic for the unanimous decision victory.

2. Frank Shamrock vs. Tito Ortiz

September 24, 1999
UFC 22

This is regarded as one of the best fights that ever took place below the UFC banner.

It was two titans at the height of their powers. Shamrock survived a battle of attrition to outlast the larger Ortiz. More slow burn than slugfest, it culminated with a bang when Ortiz tapped to Shamrock’s relentless strikes.

It was the fourth and final defense for the UFC’s first light heavyweight champion (though it was then referred to as the middleweight championship). Shamrock retired from the UFC not long after the victory.

1. Royce Gracie vs. Kazushi Sakuraba

May 1, 2000
Pride Openweight Grand Prix Quarterfinal

Special rules were set for this one, which went down during Pride’s Open Weight Grand Prix in 2000. No time limit. No judges. A throwback fight for two throwback fighters.

A boatload of highly entertaining hype ensued between the ultra-intense Gracie and the affable Sakuraba. Then, after 90 minutes and six grueling rounds, Gracie’s corner threw in the towel for Royce, who was limping and badly hurt from Sakuraba’s thudding leg kicks.

It was a crippling blow for one legend, and a legacy-building performance for the one who became known as “The Gracie Hunter.”