UFC 141 Lesnar vs Overeem: 20 Most Memorable Heavyweight Clashes of All Time

On New Years Eve 2011, UFC 141 is set to offer up one of the most anticipated heavyweight mixed martial arts fight s of all time when hulking former champion Brock Lesnar welcomes fellow behemoth Alistair Overeem into the UFC.

A combined 521 pounds will clash when these two meet at the MGM Grand Garden Arena in Las Vegas in what is sure to be an amazing battle of size and strength.

In anticipation of two of the biggest men in the world doing battle and on the heels of UFC on Fox 1 where the two best heavyweights fought for the title, what are the most memorable heavyweight matches in MMA history?

Some fights are memorable because of the build up, some fights are memorable because of the importance of the event and some are memorable because of the fight itself. Combine all these factors equally and here is my list of the 20 most memorable heavyweight fights of all time.

20. Dan Henderson vs Fedor Emelianenko

Dan Henderson vs Fedor Emelianenko

Strikeforce Fedor vs Henderson—Hoffman Estates Illinois, July 30, 2011

Henderson defeats Emelianenko via KO/TKO at 4:12 Round 1

Fedor's legend was on the decline and he came into this fight on a two fight losing streak. Henderson, on the other hand, was riding a two-fight winning streak and career resurgence at 40 years old. Emelianenko came in with a considerable size advantage

These two legends of Pride/MMA got after it right away with each fighter swinging for the knockout early and it was Henderson who landed and backed up Fedor first. Henderson pressed aggressively swinging for the knockout blow but Emelianenko defended and regained his wits.

When the two exchanged again, Fedor connected twice and dropped Henderson to the floor, following him down there to try and finish the fight. In a furious scramble on the ground, Henderson caught Fedor with a surprise uppercut from underneath and hurt the Russian badly before ending the fight with a flurry of punches.

19. Mirko Filipovic vs Aleksander Emelianenko

Mirko Filipovic vs Aleksander Emelianenko

Pride Final Conflict 2004—Superdome Saitama, Japan—August 15, 2004

Filipovic defeats Emelianenko via KO/TKO at 2:09 Round 1

The two combatants were fighting for a spot in the finals and the older Emelianenko came out stalking Cro Cop and closing the distance. He threw looping punches at Mirko trying to take him out early and Cro Cop back pedalled and defended in the early going.

Cro Cop started to fire back on the bigger opponent but Emelienenko kept plodding forward taking leg kick after leg kick as a set up for what was to come. Two minutes into the fight, Cro Cop unleashed his trademark head kick and landed it on the button, dropping the big man to end the fight.

18. Randy Couture vs Vitor Belfort I

Randy Couture vs Vitor Belfort I

UFC 15—Bay St. Louis, Mississippi—October 17, 1997

Couture defeats Belfort via KO/TKO at 8:16 Round 1

This fight was a coming out party for Couture as no one gave him a chance against the young "Phenom" Belfort. Couture made it clear that he wanted to take this fight to the ground, while Belfort was one of the most feared strikers in the world at the time.

Couture walfed right through an early barrage from Belfort and used the cage, clinch and superior dirty boxing to dominate and break the will of the younger fighter. The 34-year-old Couture pulls of one of the first of his many huge upset victories inside the octagon in his career, taking the mantle of man to beat in the heavyweight division. 

17. Frank Mir vs Antonio Rodrigo Nogueira II

Frank Mir vs Antonio Rodrigo Nogueira II

UFC 140—Toronto, Ontario Canada—December 10, 2011

Mir defeats Nogueira via kimura submission at 3:38 Round 1

In a rematch required to prove that the first fight in 2008 was no fluke, Frank Mir and Antonio Rodrigo Nogueira fought for a second time on December 10, 2011 in Toronto. Mir knocked out Big Nog in the first meeting, but his win was quickly overshadowed by talk of Nogueira injuries.

In this meeting, after nearly gettiing knocked out by a solid Nogueira right hand, Mir would make no mistake in teaching the Brazilian a painful lesson as he submitted him via kimura lock at 3:38 of the first round. The finish was one of the most gruesome in UFC history as Nogueira refused to tap out and Mir damaged Nogueira's arm badly.

16. Mirko Filipovic vs Josh Barnett II

Mirko Filipovic vs Josh Barnett II

Pride 30 Fully Loaded—Saitama, Japan—October 23, 2005

Filipovic defeats Barnett via decision after Round 3

Mirko Filipovic was kryptonite for Josh Barnett throughout his career as he defeated Barnett three times in the Pride fighting organization. Barnett was stopped twice by Filipovic, but in this their second meeting, the two went the distance in a memorable fight.

The opposite of the expected happened as Cro Cop continually took Barnett down in this one and Barnett seemed to want to keep it standing. Cro Cop was too much in top position and he dominated Barnett using wrestling and top control and took an easy decision win.  

15. Randy Couture vs Gabriel Gonzaga

Randy Couture vs Gabriel Gonzaga

UFC 74 Respect—Las Vegas, Nevada—August 25, 2007

Couture defeats Gonzaga via KO/TKO at 1:37 Round 3

In a title fight that many thought would send him back into retirement Randy Couture took on Brazilian beast Gabriel Gonzaga at UFC 74. Gonzaga was coming off a vicious head kick knockout of Mirko Cro Cop in his previous fight. Many thought he would dominate the older Couture and take the title.

In the end, Couture pulled off another amazing upset victory against Gonzaga, overcoming an early broken arm to go on and defeat Gonzaga. In the key sequence in the fight Couture picked up Gonzaga and slammed him down hard with his shoulder breaking Gonzaga's nose in the process.

It was the beginning of the end for Gabriel as his breathing was hindered from there on out and couture ended it with some ground-and-pound.

14. Cain Velasquez vs Brock Lesnar

Cain Velasquez vs Brock Lesnar

UFC 121 Lesnar vs Velasquez—Anaheim, California—October 23, 2010

Velasquez beats Lesnar via KO/TKO at 4:12 Round 1

Brock Lesnar put his title on the line against Cain Velasquez in what was a highly anticipated and evenly matched fight going in. Lesnar had a 20- to 30-pound size advantage on Velasquez, but that didn't stop the Mexican-American wrestler from San Jose.

Velasquez came out with his well rounded game. After being taken down by Lesnar, he got up and put his hands on him, landing a few shots before sending the champion reeling across the cage hurt. Velasquez tracked Lesnar down and continued the punching barrage and ending the bout at 4:12 of the first round.

Velasquez was the new heavyweight champion and has since lost the title to Junior Dos Santos.

13. Cheick Kongo vs Pat Barry

Cheick Kongo vs Pat Barry

UFC On Versus 4 Barry vs Kongo—Pittsburgh, Pennsylvania—October 23, 2010

Kongo beats Barry via KO/TKO at 2:39 Round 1

In a great example of how some fights can come out of nowhere and be most memorable, Cheick Kongo vs Pat Barry is one for the ages. Barry had Kongo hurt and on the brink of being out cold when someway and somehow, Kongo gained enough wits to throw one shot in desperation.

The shot nailed Barry on his way in and knocked him out cold to give Kongo the incredible and improbable win. 

12. Frank Mir vs Tim Sylvia

Frank Mir vs Tim Sylvia

UFC 48 Payback—Las Vegas, Nevada—June 19, 2004

Mir beats Sylvia via arm bar submission at 0:50 Round 1

In a fight for the title, behemoth Tim Sylvia came out swinging quickly in this one and Mir threw some leg kicks to get the big man off of him. Syvia planted a right hand and knocked Mir down. That was the beginning of the end for the big man as Mir quickly worked off his back and secured a tight arm bar. Mir worked his leverage from the bottom and Sylvia refused to tap and Mir ended up breaking his arm before the ref came in to stop the fight,

Mir won the title and secured one of the most famous and memorable finishes in UFC history.

11. Frank Mir vs Brock Lesnar I

Brock Lesnar vs Frank Mir I

UFC 81 Breaking Point—Las Vegas, Nevada—February 2, 2008

Mir defeats Lesnar via kneebar submission at 1:30 Round 1

The first time Brock Lesnar and Frank Mir met, the hype leading up to the fight was enormous. Lesnar was considered a wrestler from the WWE and nothing more than a gimmick and Frank Mir was the first real opponent he would face.

Lesnar came out and pounced on Mir, knocking him down and fighting in his guard. After the referee stood them up due to Lesnar striking Mir in the back of the head Brock floored Mir once again. This time, Lesnar made the mistake Mir was looking for as he stood straight up and left his leg out there for the submission ace Mir to grab.

Mir hooked the llimb sending the big man sprawling to the mat and eventually tapping vigourously on Mir to let go of the hold.

10. Fedor Emelianenko vs Kevin Randleman

Fedor Emelianenko vs Kevin Randleman

Pride Critical Countdown 2004—Saitama, Japan—June 20, 2004

Emelianenko defeats Randleman via kimura submission at 1:33 Round 1

In a bout to grab the final spot in Pride Final Conflict 2004, Kevin "the Monster" Randleman came out and delivered his best takedowns and slams on Emelianenko early. But then found he himself on the bottom of a mild jiu-jitsu scramble where Fedor softened him up with blows to the head.

Randleman left his arm out there and Fedor slapped a beautiful kimura lock on him to end the bout at 1:33 of the first round, ending any doubt that Fedor could handle a big-time heavyweight wrestler.

9. Mirko Filippovic vs Wanderlei Silva II

Mirko Filipovic vs Wanderlei Silva II

Pride Final Conflict Absolute—Saitama, Japan—September 10, 2006

Mir defeats Lesnar via KO/TKO at 5:26 Round 1

In one of the most highly anticipated fights in years these two met in what turned out to be a stand-up beating. Unfortunately for Silva, he was the victim. Cro Cop landed a straight punch early that shut Silva's eye, and the fight had to be halted for the doctor to check on the eye.

When the fight resumed Cro Cop continued the assault and Silva took heavy punishment before a leg kick to the head ended it at 5:26 of the fight.

8. Cain Velasquez vs Junior Dos Santos

Cain Velasquez vs Junior Dos Santos

UFC On Fox 1 Velasquez vs Dos Santos—Anaheim, California—November 12, 2011

Dos Santos defeats Velasquez via KO/TKO at 1:04 Round 1

This one makes the list more due to what what was on the line and the build up before the fight but in the end it certainly turned out to be memorable. Velasquez was making his very first title defence after a 14-month layoff due to shoulder surgery.

Dos Santos caught Velasquez with a monster overhand right to the temple, and that was all she wrote in what was the biggest fight in the UFC's history.

7. Randy Couture vs Tim Sylvia

Randy Couture vs Tim Sylvia

UFC 68 Uprising—Columbus, Ohio—March 3, 2007

Couture defeats Sylvia via decision after 5 Rounds

At 43, Randy Couture came out of retirement to challenge Tim Sylvia for his heavyweight belt. Sylvia went into the fight undefeated in two years of competition and reigning champion.

Couture landed an overhand right only 0:08 seconds into the fight. Then, he dominated Sylvia on his way to a decision win. Couture became a three-time heavyweight champion with the win to cement his greatness in UFC history.

He would continue competing in the UFC for another four years until he retired in 2011.

6. Mirko Filipovic vs Antonio Rodrigo Nogueira

Mirko Filipovic vs Antonio Rodrigo Nogueira

Pride Final Conflict 2003—Tokyo, Japan—November 9, 2003

Nogueira defeats Filipovic via submission at 1:45 Round 2

It was very clear early in this one that Nogueira wanted it to go to the ground, and he ended up pulling guard to get it there in the first round. Cro Cop did some punching from the top early on, but Nog defended well for most and to end the round. Cro Cop ended up getting up form Nogueira's guard.

In a grueling ten-minute second round saw the fight go to the ground right away and after a scramble, Nogueira ended up in dominant position on Cro Cop. Nogueira softened him up with punches enough to initiate a scramble and he ended up with an arm in the process. It was a masterful performance by Nogueira and the start of his legend in Pride FC.

5. Don Frye vs Yoshihiro Takayama

Don Frye vs Yoshihiro Takayama

Pride 21 Demolition—Saitama, Japan—June 23, 2003

Frye defeats Takayama via KO/TKO at 6:10 Round 1

In a match that delivered more action than anyone could expect, these two took part in an absolute brawl best described as a hockey style fight. The two punchers grabbed the back of each others heads and just wailed away with punch after punch in some of the most no-holds-barred-action in MMA history.

Frye ended up doing a ton of damage to the Japanese fighter, and Takayama was left bloody and beaten before the referee stepped in and stopped the contest six minutes in.

4. Randy Couture vs Antonio Rodrigo Nogueira

Randy Couture vs Antonio Rodrigo Nogueira

UFC 102 Couture vs Nogueira—Portland, Oregon—August 29, 2009

Nogueira defeats Couture via decision after Round 3

UFC 102 finally saw these two legendary warriors face off after many years of false starts and teasers for this fight. The two fighters were both coming off losses but the stylistic matchup was more intriguing then the title implications and the two men did not disappoint.

They went at it in an absolute war where they traded punches and blows throughout the match with both fighters getting hurt at some point in the match. The fight went from stand-up to ground battle and back and forth many times in the three rounds with Nogueira seemingly having Couture on the brink a couple of times.

Nogueira was able to maintain his pace longer. He had Couture in a d'arce choke and also a triangle choke at separate times in the fight. Couture was able to withstand both to finish out the fight.

3. Fedor Emelianenko vs Antonio Rodrigo Nogueira I

Fedor Emelianenko vs Antonio Rodrigo Nogueira I

Pride 25 Body Blow—Yokohama, Japan—March 16, 2003

Emelianenko defeats Nogueira via decision after Round 3

After winning the Pride heavyweight title in 2001, Nogueira went on a dominant five-fight winning streak before his first meeting with Fedor at Pride 25. Fedor was on an impressive streak himself, and it set up the most anticipated heavyweight match of all time in March of 2003.

Fedor came out in an aggressive onslaught putting Nogueira on the defensive throughout the first round. Nogueira could not mount any attack on Fedor due to constantly having to defend against the Russian. Fedor punished Nogueira from inside his guard and inflicted a tremendous amount of damage on the Brazilian.

The second round saw much of the same as Nogueira failed to take Fedor down and found himself on his back with Fedor pounding away from the top position. The third round was exactly the same and Fedor went on to a dominant decision win. The win started Fedor's reign as the most dominant heavyweight in the world for the next few years.

2. Randy Couture vs Pedro Rizzo I

Randy Couture vs Pedro Rizzo I

UFC 31 Locked and Loaded—Atlantic City, New Jersey—May 4, 2001

Couture defeats Rizzo via decision after Round 5

After winning back to back fights against Dan Severn and Josh Barnett, Pedro Rizzo was widely regarded as the best heavyweight in the world in 2001. The only person standing between Rizzo and the title was newcomer Randy Couture.

The fight started with a clinch battle for the ages until Couture got Rizzo down and punished him with ground and pound cutting him and taking the first round. The second round would see Rizzo damage and hurt Couture with deadly leg kicks and punches and Couture would later say it was the most damage he had ever taken in a fight.

The third round was a close battle with Rizzo continuing to score with leg kicks before Couture would take him down and dominate the second half of the round. The fourth round saw Couture begin to take over with his conditioning and Rizzo wilt under the constant pressure.

In the last round, a tentative Rizzo was controlled by Couture, who went on to gain the unanimous decision victory in one of the most grueling battles in heavyweight history.

1. Fedor Emelianenko vs Mirko Filipovic

Fedor Emelianenko vs Mirko Filipovic

Pride Final Conflict 2005—Saitama, Japan—August 28, 2005

Emelianenko defeats Filipovic via decision after Round 3

Fedor Emelianenko was in the midst of the most dominant run in heavyweight history when he met Mirko Filipovic in the most highly anticipated mixed martial arts fight of all time. Fedor was the undefeated Pride champion for three years running. Cro Cop was long said to be the man to end his reign.

The fight started and Fedor implemented a pressure game plan, backing Cro Cop up and distracting his entire striking rhythm. Cro Cop was able to land a couple hard shots in the round and bloodied up Fedor's nose, but the Russian's forward game plan was already starting to pay dividends as he grounded Cro Cop and battered him from the top to end the round.

Emelianenko started the second round winning the stand up against a visibly tired Cro Cop before taking him down for some ground-and-pound again. Fedor made Cro cop tire even more with his relentless pressure from the top, and took complete control of the fight in round two.

The third round was much of the same as Fedor took Cro Cop down at will and also won all the standing exchanges when the two were forced back to the feet. It was a very exciting fight, although Fedor would take an easy decision win.

With the win Emelianenko solidified himself as the best fighter on the planet at the time, and he would go on another five years before tasting defeat.

Dwight Wakabayashi is a Featured Columnist for Bleacher Report MMA and correspondent for MMACanada.net.

Catch him on Facebook and Twitter at wakafightermma.