In celebration of the UFC's 20th anniversary, we're counting down the UFC's greatest moments both inside and outside the Octagon with a new Top 20 each day leading up to UFC 167. Today, we give you the 20 most memorable fights in the history of the UFC.After 250 UFC events and thousands of fights, there was much to sort through and pick from. Yet, 20 wars in particular rose above the others as shining examples of the excitement and unpredictability of mixed martial arts.
Whether it was a battle between two larger than life behemoths, an epic clash for UFC gold or heated rivals whose animosity was only out-done by the fight itself, every bout that made it into the Top 20 has something special that sets it apart from the rest.
These are the fights that capitivated us. These are the fights that made us life-long UFC fans. These are the Top 20 fights in UFC history.
No. 20: St-Pierre vs. Penn I — UFC 58

After his first career loss to Matt Hughes, Georges St-Pierre rebounded with ferocity, slicing his way through four straight opponents. It became clear that he was already a force to be reckoned with, as no one seemed likely to match his combination of speed, athleticism and technique.
As he neared the top of the division and a collision course with Hughes, a surprise roadblock was thrown into his path.
B.J. Penn had left the UFC for two years starting in 2004, citing a lack of quality competition. During his break, he competed above his natural weight class, even fighting Lyoto Machida in open weight competition. But in early 2006, as the talent ranks began to swell, he returned, and was immediately thrust into the welterweight title picture when Dana White announced he’d fight St-Pierre in a top contenders fight.
The result was one of the most hotly contested decisions in years. Penn bloodied St-Pierre’s face early by finding it with long-range striking. As the fight continued on, he continually found the mark, but with less frequency, and the momentum began to shift GSP’s way, as he managed takedowns and ground work. Minute by minute, you could see Penn’s exhaustion set in and St-Pierre begin to take over.
By the end, St-Pierre’s face was a mess, and Penn looked mostly unmarked, but on the strength of his late volume, St-Pierre was declared a split-decision winner in the three-round war. The controversy helped pave the way for an eventual rematch at UFC 94.
No. 19: Jackson vs. Henderson — UFC 75

When the UFC bought PRIDE’s assets in 2007, one of its major acquisitions was the contract of Dan Henderson, who wore the promotion’s 183- and 205-pound belts, making him the only man ever to simultaneously hold major titles in two weight classes.
When he arrived, the possibilities were endless, but a champion vs. champion encounter was a no-brainer. He was matched with newly crowned UFC light-heavyweight champion Quinton “Rampage” Jackson, who had just earned the belt with a knockout of company posterboy Chuck Liddell.
The two squared off in London, and aired on free TV in the U.S., drawing an audience that reached nearly 6 million at its peak.
The fight itself was a classic, with both men favoring their traditional power punching styles. But given their durable chins, it was a chore to get either to give ground. Henderson pushed the pace early, scoring takedowns in each of the first two rounds, but Jackson’s conditioning was on point, as the fight wore on, he continued his volume striking, stuffed most of Henderson’s takedown tries, and landed the bigger power punches, even knocking Henderson down in the fourth. The fifth was a war of attrition, with the result likely hanging in the balance. With the belts on the line, Jackson out-landed Henderson 31-19 and scored a late takedown to clinch it.
The win made Rampage the first man to unify the UFC and PRIDE titles.
No. 18: Lesnar vs. Carwin — UFC 116

For those who have never experienced it, there is nothing like a heavyweight championship prizefight in Las Vegas between two fighters with the aura of near-invincibility surrounding them. That was exactly the setting in July 2010, when behemoths Brock Lesnar and Shane Carwin settled the question of the UFC’s best big man.
At the time of the meeting, Carwin had been on an absolute rampage, with 12 pro fights and 12 first-round finishes. In his most recent fight, he’d destroyed Frank Mir, bludgeoning him in the corner with thunderous punches that seemed to shake the cage. Meanwhile, the champion Lesnar was returning from diverticulitis, a digestive disease that forced him to undergo emergency surgery to have a piece of his colon removed. While Lesnar’s career was threatened, he returned within a year and stepped right into the match with Carwin.
With a sold-out MGM Grand Garden Arena buzzing, the two titans met, and in the opening round, it seemed that Carwin would continue his run, avoiding Lesnar’s early takedown tries and then knocking him down with a barrage against the fence. For the next two minutes, Carwin would unload, looking for the finish. Somehow, Lesnar held on, defended, and returned to his feet, surviving the round.
As he waited for the start of the second round, Lesnar winked at Carwin, then quickly took him down, passed his guard and tapped Carwin out with an arm triangle.
No. 17: Shamrock vs. Ortiz — UFC 22

To many of the sport’s observers, Frank Shamrock was among the first fully formed mixed martial artists, an athlete capable of striking, wrestling or grappling with the best of those respective disciplines.
His abilities were put to the test at UFC 22, where he took on the bigger, stronger Tito Ortiz. Shamrock had won the belt in 1997, and defended it three times when Ortiz was granted the title shot against him.
For the first three rounds, Ortiz did what he did best in his heyday, taking the fight to the ground, utilizing elbow strikes and attempting to wear down his opponent. But Shamrock’s conditioning was impeccable, and he stayed just as busy whether the fight was standing or on the ground (the final striking stats, for example, favored Shamrock 193-67).
As the fight wore on, Ortiz’s output began to lessen. In the fourth, Shamrock took the center of the cage and landed at will. Ortiz managed a desperation takedown midway through but towards the end of the round, Shamrock worked his way up, soon threatened with a guillotine and pounded a downed Ortiz with elbows and hammerfists until Ortiz tapped, ending one of the sport’s first classics.

No. 16: Hughes vs. Penn II — UFC 63

When Matt Hughes and BJ Penn fought the first time at UFC 46, Penn had won as an underdog, capturing his first title. Over two years later, Georges St-Pierre was scheduled to fight Hughes when he was injured, allowing Penn to step in as a replacement.
A rematch between the two had always been anticipated, and the championship at stake only added to the intrigue. As he did in the first fight, Penn seized control early, shutting down Hughes’ vaunted wrestling game -- he stopped his first seven takedown tries -- and battering him on the feet. But Hughes was never really out of a fight, and everyone knew it.
During a second-round scramble when Penn was trying to take Hughes’ back, he hurt a rib, and when he came out for the third, he wasn’t the same. No one knew of his injury at the time, but he was almost completely out of gas against a fighter who seemed to have a limitless tank. Almost immediately, Hughes took over and eventually got the fight to the ground where he trapped Penn in a crucifix, raining down blows until the referee had to save Penn. The win evened the series and eventually led to a trilogy fight.

No. 15: Condit vs. MacDonald — UFC 115

Carlos Condit needed to be on this list somewhere, didn’t he? One of the UFC’s all-time fiercest competitors, he’s been involved in several excellent matches over the years, but with apologies to his near knockout of Georges St-Pierre at UFC 154, perhaps none was more thrilling than his June 2010 bout with wunderkind Rory MacDonald.
At the time, MacDonald was only in his second UFC bout, but he took it to Condit early with his wrestling advantage, taking him down three times in the first round alone. In the second, Condit seemed to solve the wrestling question, but MacDonald still found success in the standup with his power, but it was the third when Condit came alive.
Digging deep, he won a scramble and pounded MacDonald from top position. While the youngster worked his way up, Condit took him back down and resumed the beating, hammering him with elbows and punches. Given the first two rounds, it appeared Condit needed a finish, and time was running low as the exhausted MacDonald just tried to survive. Finally, as the 10-second warning sounded, it seemed he would, but Condit’s relentless assault continued, until it was too much. Referee Kevin Dornan stopped the action with seven seconds remaining to end a dramatic comeback.

No. 14: Couture vs. Sylvia — UFC 68

In February 2006, Randy Couture and Chuck Liddell fought for the third and final time. Liddell, in the midst of his light-heavyweight title run, knocked out Couture in the second round, and afterward, the 42-year-old Couture called it quits.
After doing some acting and fight commentating, Couture got the itch to compete, and in a surprise, announced he’d return. Just as surprisingly, he said he would move up in weight to face the heavyweight champion Tim Sylvia in March, a little over a year after he’d hung up his gloves. At the time, Sylvia had a 23-2 record and had won six straight fights, leading oddsmakers to paint him as a 3-to-1 favorite.
Instead, it was Couture from bell to bell. The fight is most remembered for its opening sequence, which saw the legend drop the giant with his very first punch of the fight, an overhand right. For a moment, it seemed as though Couture would finish him in seconds, but Sylvia was able to hang on, though just barely. The rest of the fight was a mauling. Couture took Sylvia down seven times, out-landed him by nearly 100 strikes, and swept the judges’ scorecards.
At the age of 43, Couture had shockingly become the UFC’s oldest champion.

No. 13: Silva vs. Stann — UFC on FUEL TV 8

Every great warrior seems to have one last stand, a moment where he turns back time and bucks the odds to win.
For Wanderlei Silva, that moment might have come against Brian Stann at UFC on FUEL 8. Silva had come into the fight losing two of his last three, with his lone win coming against Cung Le, who was 39 years old and coming off a one-year layoff.
Against the younger, stronger, faster Stann, Silva was deemed the underdog. After all, there was some question about whether Silva could take punches the same we he used to, and Stann was best known for his heavy hands. Silva had also been injury prone.
With that as the backdrop, the first round went almost exactly as expected. Stann was willing to play SIlva’s berserker game, but at a faster speed. The played out during a sequence where Silva dropped him, but Stann immediately jumped back to his feet, wobbling Silva a few strikes later, then beating him up on the mat.
The pace and style though, was making Silva feel right at home, and during a frantic second-round exchange, Silva clipped Stann with a left hook behind the ear, dropping him. In an instant, he was atop his opponent, dropping right hands to the finish.
The fight turned out to be the swan song for Stann, who retired shortly afterward.

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