UFC's Greatest Hits

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A three-part series chronicling the 15 greatest moments in UFC history as the company celebrates its 15th anniversary.

UFC’s greatest hits: the early days

The Ultimate Fighting Championship debuted in Nov. 1993 in Denver, and nobody, neither the promoters nor the participants, had any idea what they were getting into.

Seconds into the first match, Gerard Gordeau, a kickboxer bouncer from The Netherlands who was more famous as a sometimes pro wrestler in Japan, literally kicked the teeth right out of the mouth of Teila Tuli, billed as a 420-pound sumo wrestler. That show created UFC’s first two stars, Royce Gracie, who won the eight-man tournament, and Ken Shamrock, who went on to become one of the most important people in the development of the sport.

Since then, the UFC has been on a 15-year-ride of cult popularity, public misunderstanding, near death, and a resurrection to the extent it is the biggest thing on pay-per-view in North America.

There have been 119 shows, all over the world. In recent years, it has set gate and merchandise records in many venues.

Yet, it is still banned in New York and Toronto, and on an international level, a lot of the media still react like the U.S. media in the 1990s, seeing it as something they simply can’t accept as a sport.

Here’s a look at five of what were not necessarily the best matches, but were the most memorable matches of the early years, before the Fertitta brothers purchased the company and president Dana White put his distinct stamp on the product.

Sept. 9, 1994: Royce Gracie’s first real challenge

After winning seven fights in a row, in two tournaments, with seeming ease, the skinny Brazilian in a bathrobe had shocked the world. He had broken down every premonition of what would happen in a fight where any style was legal and was a one-man commercial for the wonders of his fighting system, billed as Gracie jiu-jitsu.

At UFC 3 in Charlotte, Kimo Leopoldo, a muscular Hawaiian who outweighed Gracie by nearly 60 pounds, looked to be victim No. 8. But unlike his previous foes, Gracie struggled to get his foe to the ground, and had to resort to moves like hair pulling and knees to the groin, both legal at the time.

After 4:40, Leopoldo gassed out and submitted to an armbar. Gracie had prevailed once again, but the beating he took forced him to withdraw from the tournament, and it became the most talked about battle up to that point.

April 7, 1995: The first Superfight

Gracie and Ken Shamrock had become the company’s two biggest draws when they were set to meet to crown UFC’s first singles champion at UFC 5.

Instead of going through a tournament, they were put in a main event, and it drew 260,000 buys on PPV, an MMA record that stood for 10 years.

The match itself was terrible. Shamrock took Gracie down and held him there. There were no referee-ordered stand-ups in those days. Gracie couldn’t get up, and couldn’t come close on any submissions, mostly doing kidney kicks. There were no rounds, so after 30:00 of relentless inaction, it was over and they went into an overtime.

Shamrock caught Gracie with a huge right, busting him open, and they went right back to the same ground position. This time Shamrock was more aggressive with head-butts. At 36:06, the fight was called off because their three-hour allotment of television time was running out.

There were no judges in those days, and it was ruled a draw. Today, it would be considered a horrible fight. The match left bitterness on both sides and fans debated for years on who would win a rematch, which many promoters tried to put together but Gracie never accepted. Gracie stayed out of the octagon for the next 11 years, claiming time limits worked against him, but time limits were necessary for a pay-per-view product.

July 14, 1995: The next superstar

David “Tank” Abbott, with his goatee and sinister look, burst into UFC by knocking out a huge Samoan, John Matua, in seconds, and then making fun of Matua as he went into convulsions at UFC 6 in Casper, Wyoming. He went to the finals of the tournament, where he lost a dramatic battle to Russian Oleg Taktarov via choke in 17:47.

Still, even in losing, Abbott was a winner with the fans. He would brag that he was fine while Taktarov, who looked like death warmed over due to dehydration after a long battle in the high altitude, had to be hospitalized.

A tremendous talker and self-promoter, Abbott was 9-14 in his MMA career, and never beat a name fighter. But he commanded six-figure paydays right until the end, in February, when he was obliterated in 43 seconds by Kimbo Slice in Showtime’s all-time most watched bout.

July 27, 1997: Striking conclusion

By 1997, the nearly five-year-old sport had been dominated by ground fighters Gracie, Shamrock and Dan Severn. But with all of them gone, the new sensation was Mark “The Hammer” Coleman, a powerhouse former Olympic wrestler who had beaten Seven to become the UFC heavyweight champion.

At UFC 14, he was to face Maurice Smith, a legendary kickboxer in the ‘80s who figured to be past his prime and would easily be taken down and mauled, as all kickboxers, boxers and karate fighters up to that point had been. He had been champion in the rival Extreme Fighting Championship, but that group’s heavyweight division had nobody close to Coleman’s level. This so-called dream match of two champions was thought to be a foregone conclusion.

But Smith and trainer Frank Shamrock came up with a game plan. In what was a sport built on aggression, they did the new style of rope-a-dope, waiting and defending on the ground and waiting for Coleman to tire. After about 12:00, Coleman was spent, Smith spent the next nine minutes picking the exhausted Coleman apart, and Smith became the first man from a striking background to become a UFC champion.

Smith’s title reign only lasted five months. Another wrestler provided the counter to Smith’s winning strategy to where he could take him down at will, and this wrestler never gassed. His name was Randy Couture.

Sept. 24, 1999: The next stage

Smith was a striker who learned to defend on the ground. But the first true triple threat combining striking, grappling, and most of all conditioning, was Ken Shamrock’s adopted brother and former protege, Frank Shamrock.

Shamrock was brought in as cannon fodder for Olympic gold medalist Kevin Jackson, for whom the company created an under-200 pound weight class to showcase.

Shamrock beat Jackson with an armbar in 14 seconds, and spent the next two years as the top star in UFC.

At UFC 22, he faced Tito Ortiz for the middleweight (now light heavyweight) title in the last truly memorable fight of the early era.

Ortiz, who weighed in at 199, was up to 217 pounds by fight time, while Shamrock was 192 pounds, weighing in fully clothed and holding a book. The two appeared to be what today would be considered two weight classes apart.

Ortiz took Shamrock down with ease and tried ground and pound, while Shamrock, from his back, kept up a fast pace designed to tire. Unlike with Smith, whose game plan was to relax and not lose until Coleman tired, Shamrock kept moving on his back to make Ortiz work even faster.

Even though Ortiz won the first three rounds on the judges’ cards, thus almost guaranteeing him a decision, it was clear at the end of the third round that Shamrock was still fresh and Ortiz was struggling. Still, Ortiz got the takedown in round four and was en route to taking another round on the scorecards. Suddenly, late in the round, Shamrock exploded from his back, grabbed a guillotine to suck more air out of Ortiz, and finished him with strikes in what up to that point was the best comeback finish in UFC history.

Shamrock, the best all-around fighter UFC had seen up to that point, and arguably its best talker, was seen by almost nobody in his prime years. By this point, almost no cable companies carried UFC. Any real money in the sport was in Japan. Gracie, by this time, hadn’t fought in four years. Ken Shamrock was a successful pro wrestler in WWF, while Severn and Abbott were also pro wrestling. Both were not as successful as Shamrock, but in the case of Abbott, like always, he came in with a great contract and made a lot of money at it. Smith and Coleman were fighting in Japan, where the sport was a few months away from becoming a phenomenon. UFC appeared to be limping to a very quiet death.

UFC’s greatest hits: the middle years

In early 2001, the Ultimate Fighting Championship, a business barely clinging to existence as it was run by a tapped-out Bob Meyrowitz, was sold to casino magnates Lorenzo and Frank Fertitta, the latter a former member of the Nevada State Athletic commission, who put high school friend Dana White in charge.

The UFC’s financial issues were thought to be largely because virtually every major pay–per-view carrier refused to air the events. The 1994-96 success of the company built around Ken Shamrock, Royce Gracie, Dan Severn and David “Tank” Abbott, wasn’t a gimmick that ran out of steam as much as something that fell because the shows weren’t available to most of its fans, who moved on to other things.

In 2001, when the company was purchased, the belief was that once they got back on pay-per-view, the early success would be repeated. As it turned out, that wasn’t the case, and the company, by its own accounts, lost about $33 million from 2001-05 until the magic ingredient, “The Ultimate Fighter” reality show, turned their fortunes around.

The most memorable matches of that struggling period were:

May 4, 2001: Randy Couture vs. Pedro Rizzo

Couture at this point was the heavyweight champion. He was almost 38 at this point, and Rizzo, with a good sprawl, savage leg kicks and good hands, was believed to be the next big star. Zuffa thought so much of him that he was signed to a $175,000 per-fight contract, making him the highest paid fighter in the promotion. This fight in Atlantic City was one of UFC’s best back-and-forth matches in history. Couture shockingly destroyed Rizzo, taking him to the ground and pounding him out with Rizzo bleeding and barely defending. In fact, many were critical of ref John McCarthy for not stopping the fight, and the horn clearly saved Rizzo from what appeared to be certain defeat.

The second round was reversed, as Rizzo came back and was on the verge of winning. Couture was on his knees, putting up no defense, and for some reason, Rizzo paused rather than throw what could have been the finishing punch, and time ran out.

Rounds three and four saw two completely spent fighters in slow-motion battling like wounded animals just trying to survive. Couture took Rizzo down in both rounds and did minimal damage, but it was enough to win both rounds, and ended up making the difference in the fight. Rizzo took control in the last ten seconds of the fifth round and seemed on the verge of defeat when time ran out. Couture got a decision that could have gone either way, although more felt it went the wrong way. In fact, Frank Shamrock, announcing at the time, when Couture’s hand was raised, asked what fight the judges were watching. A rematch was set up for November 2, 2001. Couture conclusively answered the question as to who should be the champion, as he dominated the second meeting.

Nov. 2, 2001: Matt Hughes vs. Carlos Newton:

This match in Las Vegas is famous for the most unique title-change finish in UFC history. Newton was defending the welterweight title that he had won from Hughes’ coach, Pat Miletich. A hot first round saw Hughes score with high slams, but Newton was able to reverse him twice on the ground. During the second round, Newton clamped on a triangle and looked to have the match wrapped up.

Hughes picked Newton up from that position while caught in the move, draped him on top of the cage, paused, and planed him with one of the hardest pro wrestling power bombs you’ll ever see. Newton was knocked cold by the move, and ref McCarthy saw it, and stopped the fight, not noticing that Hughes had actually passed out at the same time from the triangle. By the time McCarthy turned around, Hughes had recovered and the look on his face when he was told that he won was priceless. He had no clue what had happened or that he had just won the championship. Like with Couture-Rizzo, a rematch was held on March 13, 2002, in London, England, and Hughes won this one conclusively.

Nov. 22, 2002: Tito Ortiz vs. Ken Shamrock:

This was one of the key matches in history, because UFC was losing money and gaining no ground. When the Fertittas purchased the company in early 2001, the belief was they would start at around 100,000 buys on pay-per-view, and grow to the level the company was doing in its 1994-96 heyday. The reality was different. The first pay-per-view event was a disaster, with every match going to a decision and time running out in the middle of the main event, leading to massive refunds.

Subsequent shows were doing 35,000-50,000 buys and showing no sign of growth. It was looking like a bad investment, when the decision was made to bring back Shamrock, an early star who had become even more famous after three years as a star during a period when pro wrestling was having its most mainstream success. Between clips of Shamrock waving his finger at Ortiz, and Ortiz flipping off Shamrock after beating one of his proteges from 1999, Zuffa had its first grudge match with well-known names.

After the two went after each other on “The Best Damn Sports Show Period,” the result was the company’s first sellout at the MGM Grand Garden Arena, the first million-dollar gate, and 150,000 buys on pay-per-view. Shamrock, fighting with a torn ACL, stunned Ortiz with a punch early. But for most of the fight, the younger Ortiz was too quick for the 38-year-old Shamrock, massacring him before Shamrock, his face a mass of cuts and bruises, asked out and McCarthy stopped the fight.

The success of this match gave hope that UFC could be a success. The bad news was, most of the people who bought this show, didn’t come back, and it wasn’t until 2005 before the company became a pay-per-view success.

Shamrock and Ortiz had two more matches, both won by Ortiz, in 2006, that caught the attention of the mainstream sports world with the pay-per-view numbers of the first (775,000 buys), and the TV ratings of the second (still the highest rated cable MMA special). Even though the three matches were one-sided, it was without a doubt the most important series of matches in company history.

Sept. 26, 2003: Tito Ortiz vs. Randy Couture

Ortiz, as light heavyweight champion, kept coming up with reasons not to face Chuck Liddell, the top challenger. By the spring of 2003, Dana White had enough, and created the first interim championship, pitting Liddell against Couture, with Couture moving down from heavyweight.

Couture had lost two fights in a row and the company believed Liddell was its next big star, but Couture spoiled Liddell’s coronation by stopping him on June 6, 2003. Suddenly, with Couture as the interim champion, Ortiz was ready to come back. The normally calm Couture responded to Ortiz’s trash talking to show a new-found personality edge. The dynamic led to Couture becoming one of the most popular fighters in UFC history, as people wanted to see Ortiz get his mouth shut. Couture was the father teaching the son a lesson in respect, outwrestling him for five straight rounds, and in a moment that couldn’t have been scripted any better, literally turned Ortiz over and spanked him with seconds remaining, as Couture won the first of his three championships past the age of 40.

April 9, 2005: Forrest Griffin vs. Stephan Bonnar

Dubbed by White the most important fight in UFC history, this was the light heavyweight final of the first season of The Ultimate Fighter, and more important, the first time UFC ever aired live on television. It was the perfect fight on the right night. Griffin and Bonnar threw down for three straight rounds. Griffin won the first round. Bonnar solidly won the second round. The third round was even, with Griffin outstriking Bonnar in the last minute to win a 29-28 decision that really could have gone either way.

The emotion was incredible as the fight ended, particularly as White proclaimed that there was no loser in that fight, and gave Bonnar the same winner’s contract that Griffin got. UFC had spent $10 million in production costs on the season in a last-ditch effort to get the sport rolling. The first season was an experiment. Immediately after this match, Spike TV signed UFC to a long-term deal. A week later Couture and Liddell set the company record with 280,000 buys on pay-per-view. The UFC’s growth was about to skyrocket.

UFC’s greatest hits: The modern era

Unlike the boom period of the mid-1990s with its underground feel, and the struggling early years of the Zuffa LLC era before getting on cable television, the following five fights were huge pay-per-view and live events.

(One note on this list. We didn’t include the Brock Lesnar’s UFC heavyweight championship win over Randy Couture, because it technically came a few days after the actual 15th anniversary).

May 27, 2006: Royce Gracie vs. Matt Hughes

When the UFC started in 1993, its first tournament champion was Gracie, who revolutionized fighting by showing the importance of the ground game, and in particular, submissions, to a public that largely thought a real fight without boundaries would feature two heavy hitters slugging away.

Gracie stopped fighting in the UFC after his 1995 rematch with Ken Shamrock. He returned in 2000 to fight in Japan, including a legendary loss to Kazushi Sakuraba in a no time limit match that went 90 minutes before Gracie’s corner threw in the towel.

The promotion of the sport’s original legend against Hughes, the dominant welterweight fighter of the era, was among the best jobs UFC has ever done. They made the match seem far more competitive than logically should have been expected.

Commercials in which Gracie talked of UFC being “his house,” and how he was going to take the current star, choke him out, and send him home, were contrasted by Hughes saying Gracie’s style was out of date. The hype made for the first UFC show to crack 600,000 buys on pay-per-view.

While most insiders recognized Gracie, 39, stood little chance in the fight, fans hotly debated the issue. Most had not only never seen Gracie’s fights in Japan where it was clear his days of domination were long over, but had never even heard of them. Most thought that nobody had ever beaten Gracie, and he was billed in the commercials as undefeated in the octagon, which wasn’t a straight-up lie, but was misleading, as the Sakuraba fight was in a ring.

Then-welterweight champion Hughes, while dominant, had at least proven beatable, leading people to think Gracie had a chance in their Los Angeles fight.

But it was a different game, with better, more skilled and further evolved athletes. Hughes caught Gracie in a straight armbar early, but when he saw Gracie wouldn’t tap, he got his back, and fired punch after punch. After 17 of the blows, ref John McCarthy stopped the fight in 4:39. This match showed that the days of dominating with Brazilian jiu-jitsu and no other skills were over.

December 30, 2006: Chuck Liddell vs. Tito Ortiz

In many ways, this fight was the single event popularity peak of UFC. Ortiz had just set an MMA pay-per-view record and then an MMA television ratings record in two easy wins over Ken Shamrock. Nobody was neutral about Ortiz. Some loved him for his charisma. Others hated him for his brashness and wanted to see Liddell, the light heavyweight champion, shut him up. Most expected that result, since Liddell had knocked Ortiz out the first time they met.

The match at the MGM Grand in Las Vegas did just over 1 million buys. With the exception of boxing matches involving Oscar De La Hoya, Mike Tyson or Evander Holyfield, more Americans purchased this pay-per-view than any othyer sporting event in history. It was a buzz in Las Vegas that UFC has come close to a few times, but never quite matched.

The key was whether Ortiz would be able to take Liddell down, because standing, Liddell had the distinct edge. In round one, Liddell got the mental edge when Ortiz couldn’t take him down. Late in the round, Liddell struck, opening up two cuts with punches, and knocking Ortiz down late in the round, and nearly finished him. Ortiz finally got a takedown and Liddell’s back in round two, winning the round.

In the third round, Liddell opened the cuts worse, and then as Ortiz decided to trade, Liddell knocked him down, with a rapid flurry of punches on the downed Ortiz, referee Mario Yamasaki stepped in. UFC had its biggest spotlight in history shined down on this night, and Liddell emerged, indisputably, as its brightest star.

March 3, 2007: Tim Sylvia vs. Randy Couture

If Ortiz vs. Liddell was the UFC’s business peak, Sylvia vs. Couture was the emotional peak. Held in Columbus, Ohio, Couture had retired one year earlier after being knocked out by Liddell.

UFC was in a quandary at the time. Brandon Vera, who was being groomed to be the next heavyweight star, was in a contract dispute and turned down the shot at the 6-8, 265-pound Sylvia. UFC was looking at disastrous pay-per-view numbers if they put Sylvia in with Gabriel Gonzaga, which seemed the alternative. Instead, Couture, who had been knocked out in two of his previous three fights as light heavyweight, and was a few months shy of his 44th birthday, agreed to come out of retirement.

Couture was giving away 13 years in age, eight inches in height, 12 inches in reach, and at least 41 pounds.

At the seven-second mark, Couture came over the top with the hardest overhand right of his career, and Sylvia went down to the loudest crowd reaction in UFC history. While Couture never came close to finishing the fight, he dominated all five rounds, and with time running out, the crowd counted down like New Year’s had come early. They took their celebration to the streets after the match like no UFC bout in history.

December 29, 2007: Wanderlei Silva vs. Chuck Liddell

For years, this was the dream fight that never happened. Silva dominated Japan, with an unprecedented six-year reign as 205-lb. champion with the PRIDE organization, where he headlined several events that sold out the 55,000-seat Tokyo Dome. Liddell was UFC’s biggest star. Dana White tried to put the match together in 2003, putting Liddell in a PRIDE tournament, but Liddell lost in the semifinals to Quinton Jackson, who Silva then finished in the finals.

In the summer of 2006, PRIDE promised the match of champions to UFC, but the deal fell apart as PRIDE instead decided to run in the U.S. in opposition to UFC. Then PRIDE fell into financial disarray, and was about to sell to UFC, and White was salivating at putting together his personal dream match.

But before the sale went through, Silva fought Dan Henderson on a PRIDE card in Las Vegas, and got knocked out, losing his championship. UFC president White was furious, thinking the biggest match in history had been ruined. Then Liddell got knocked out by Jackson at UFC 71 and lost his title.

In September of 2007, with Silva signed to UFC and watching at ringside and the dream match ready to be announced, Liddell lost via decision to Keith Jardine.

White was distraught, thinking the match would never happen, but then decided to make it anyway. Both men were coming off two straight losses, and Silva’s losses were by brutal knockout.

But the match at UFC 79 in Las Vegas was everything people had hoped for years to see. Both men went a fast-paced three rounds, trading crisp, brutal shots. Unlike the usual, predictable Liddell who would sit back and look for the knockout shot, on this night Liddell combined kicks and takedowns, keeping Silva off balance.

The second round, in particular, was one of the year’s best, and Silva scored one clear knockdown and Liddell went down a second time from a combination slip and punch. But Liddell took over in round three, and scored a takedown with 20 seconds left to ice the fight.

April 19, 2008: Matt Serra vs. Georges St. Pierre

This was a night where what seemed like a disaster for St. Pierre a year earlier, ended up in storybook fashion.

Serra, a tough UFC journeyman lightweight fighter, barely won a tournament on The Ultimate Fighter reality show, in the welterweight class. An 8-to-1 underdog against St. Pierre, he seemed to be one of the few people on Earth who thought the idea of the match being for the title wasn’t a joke. Then he knocked St. Pierre out at UFC 67 in Houston and claimed the title.

The rematch came at UFC’s Canadian debut, at the Bell Centre in Montreal, not far from St. Pierre’s home just outside the city. The show sold out immediately, with a UFC record 21,390 fans coming from all over the country, as well as setting Canadian records for the most pay-per-view buys of any event in history.

Serra may have done the best job in promoting an event in UFC history, hamming up his “bad guy” role to the hilt, but once the cage door locked, St. Pierre dominated, winning with hard knees to the body on the ground, and the fight was stopped with 15 seconds left in round two.