UFC 30th anniversary: 30 memorable moments in the UFC's long and colorful history

(Stefan Milic/Yahoo Sports Illustration)

The 30th anniversary of UFC 1 is Sunday, a day after UFC 295 in Madison Square Garden in New York. The promotion has had a colorful history in those 30 years, though there were many points at which it appeared it wouldn’t survive to see a second year, a fifth year or a 10th year.

To observe the anniversary, Yahoo Sports put together a list of what it considers 30 of the top moments in UFC history.

It’s a subjective list, one that includes business deals as well as fights, and no one will agree with all of the choices or the order in which they’re ranked.

But these moments are sure to ring a bell and trigger memories of the UFC’s long and fascinating history.

30. Randy Couture defeats Tim Sylvia at UFC 68 to regain heavyweight title

Randy Couture had long since established his credentials as one of the greats in the history of MMA before this fight. He had two stints as heavyweight champion and two others as light heavyweight champ. He was also the UFC 13 tournament winner.

But going into this fight, there was legitimate concern for him from some members of the fan base. For starters, he was 43 years old and was facing a 6-foot-8 giant in Sylvia.

Couture, though, knocked Sylvia down in the first 10 seconds and went on to defeat Sylvia 50-45 on all cards to capture his final championship.

29. UFC purchases chief rival Pride

When Dana White and partners Frank and Lorenzo Fertitta purchased the UFC for $2 million in 2001 from Semaphore Entertainment Group, the UFC was playing second fiddle to the Japanese-based Pride Fighting Championships. Pride had more of the game’s big stars at that point.

But a report in Japan linked Pride’s ownership to organized crime and, as a result, the company lost its TV deal with Fuji. That prompted owner Nobuyuki Sakakibara to sell, and the UFC got the job done for $67 million.

Though plans originally were for Pride to be run as a standalone company, it was merged into the UFC and brought in a nice infusion of talent to the promotion, including Mauricio “Shogun” Rua, Robbie Lawler and Dan Henderson, among others.

28. Junior dos Santos KOs Cain Velasquez to win heavyweight title in first UFC bout on network television

The UFC wasn’t the first MMA organization to broadcast a bout live on network television. That honor went to Elite XC, which put a show on CBS featuring Kimbo Slice in 2007. But the beginning of the UFC’s deal with Fox started with a show live on the network on Nov. 12, 2011, in Anaheim, California. Junior dos Santos won the heavyweight title when he knocked out Cain Velasquez at 1:04 of the first round of their bout, the only one on the card that was broadcast on Fox.

27. Amanda Nunes KOs “Cyborg” in 51 seconds to become a double champion

Amanda Nunes had already dispatched two of women’s MMA’s most legendary fighters, Miesha Tate and Ronda Rousey, in bantamweight title fights when she agreed to move up to featherweight at UFC 232 on Dec. 29, 2018, to face the intimidating Cris “Cyborg” Justino for her title at The Forum in Inglewood, California.

Justino had won 20 in a row after losing her pro debut in 2005 and was one of the most intimidating fighters in the sport’s history. She and Nunes began slugging with each other at the opening bell and Nunes finished her in dramatic fashion with strikes in less than a minute.

That win established Nunes as the greatest women’s MMA fighter of all time and was one of the most exciting fights of that year.

26. UFC 129 draws record crowd of 55,724

If landing a network television deal with Fox a few months earlier didn’t signify that the UFC had hit the mainstream in our sporting culture, UFC 129 in Toronto on April 30, 2011, sure did.

That card, topped by a welterweight title fight between Georges St-Pierre and Jake Shields, drew 55,724 fans to Toronto’s Rogers Centre and earned a paid gate of $12.1 million, both UFC records at the time.

25. UFC hires Marc Ratner to get MMA sanctioned

Mixed martial arts was only sanctioned in 19 states in the U.S. when the UFC hired Marc Ratner from the Nevada Athletic Commission on May 15, 2006, and named him as its vice president for regulatory affairs. Ratner began visiting with state athletic commissions around the country and helped get the sport legalized throughout the U.S. (and Canada).

Hunter Campbell, the UFC’s chief business officer, said to Yahoo Sports of Ratner’s hiring, “I can assure you that [expansion] wouldn’t have happened without [Ratner].”

24. UFC 249 marks return to sports after COVID-19 pandemic

From the moment the world shut down following the COVID-19 pandemic in 2020, UFC president Dana White vowed his company would be the first to return in terms of providing a sporting event. True to his words, White put together UFC 249 on May 9, 2020, in Jacksonville, Florida, headlined by an interim lightweight title fight between Tony Ferguson and Justin Gaethje and a bantamweight title fight between Henry Cejudo and Dominick Cruz.

The card was sensational, but was held with no fans in attendance. Coming back from the pandemic first, however, seemed to push the UFC’s business success up another notch.

23. GSP loses title to Matt Serra in massive upset at UFC 69

The last loss of Georges St-Pierre’s legendary MMA career came in the main event of UFC 69, when he was knocked out in the first round by Matt Serra in what remains one of the greatest upsets in UFC history. Serra was an 11-1 underdog but cleanly finished St-Pierre.

St-Pierre was 13-1 heading into the Serra fight and was coming off impressive back-to-back wins over B.J. Penn and Matt Hughes. He avenged the loss to Serra at UFC 83 and ended his career on a 13-fight winning streak.

22. Zhang Weili, Joanna Jędrzejczyk stage greatest women’s fight ever

The hype wasn’t out of control at UFC 248 in Las Vegas on March 7, 2020, when Zhang Weili defended her women’s strawweight title against Joanna Jędrzejczyk in the co-main event that night. But they put on an incredible slugfest, clearly the best women’s fight in UFC history and one of the greatest fights ever, period.

Jędrzejczyk came out of the bout with a huge egg-sized welt on her forehead and lost lo a split decision to Zhang.

21. ‘Rampage’ wins title by knocking out ‘The Iceman’ cold

The UFC acquired the contract of popular light heavyweight Quinton “Rampage” Jackson on Dec. 11, 2006, when it purchased the assets of the World Fighting Alliance. That deal paid off big time when Jackson for the second time finished the UFC’s biggest star at the time, light heavyweight champion Chuck Liddell.

Jackson had knocked out Liddell in a Pride show in 2003. When the UFC brought him back, it was with the intention of setting up a showdown between the two heavy-handed sluggers.

Jackson cracked Liddell with a short right hand and finished him in 1:53 to end Liddell’s reign. Liddell never again held a UFC belt, and from that point on, he struggled to win. He was 20-3 heading into that bout but, including the loss to Jackson, dropped six of his final seven.

20. Matt Hughes slams Frank Trigg

Matt Hughes and Frank Trigg met in a rematch for the welterweight title at UFC 52 on April 16, 2005, at the MGM Grand Garden in Las Vegas. Hughes ended the fight with a rear naked choke submission at 4:05 of the first round, but that only tells part of the story.

Earlier in the round, Trigg hit Hughes low, but the referee didn’t see it. Hughes was in trouble and Trigg was pummeling him. He sank in a rear naked choke and seemed to be on the verge of an upset title win.

Hughes somehow managed to get out of the choke, which was in tight. He got to his feet, lifted Trigg and carried him across the Octagon. He viciously slammed Trigg, then slapped on a rear naked choke. When Trigg tapped, it produced the loudest crowd reaction in a UFC bout to that point and still one of the loudest ever.

19. Khabib Nurmagomedov retires undefeated at UFC 254

Lightweight champion Khabib Nurmagomedov choked out Justin Gaethje with a triangle choke at 1:34 of the second round on Oct. 20, 2020, in Abu Dhabi, United Arab Emirates, to retain his belt and improve his record to 29-0.

His father and coach, Abdulmanap, had died a little more than three months earlier, and Nurmagomedov was very emotional on fight day. He announced his retirement in the cage, saying his mother didn’t want him to fight anymore.

Despite efforts to lure him back, Nurmagomedov resisted and hasn’t fought since, ending one of the great careers in UFC history while still in its prime.

18. Robbie Lawler, Rory MacDonald engage in brutal slugfest

Lawler and MacDonald met for the welterweight title on July 11, 2015, in the co-main event of UFC 189 at the MGM Grand Garden in Las Vegas. It was the co-main event to the interim featherweight title bout between Conor McGregor and Chad Mendes.

Legendary singer Sinead O’Connor sang live during McGregor’s ring walk, and McGregor finished Mendes to win his first UFC title. But it was all overshadowed by the incredible battle between Lawler and MacDonald for the welterweight title.

It was an incredibly violent, back-and-forth slugfest that Lawler won by TKO at 1:00 of the fifth. MacDonald’s nose was broken and bleeding badly. Lawler cracked him on the nose again early in the fifth and MacDonald could take no more. He went down and Lawler quickly ended it.

It’s always included as one of the five greatest fights in UFC history and many have tabbed it the No. 1 bout in the promotion’s history.

17. Tito Ortiz, Ken Shamrock duel in important bout at UFC 40

Ken Shamrock was a star of the early days of UFC, but UFC 40 on Nov. 22, 2002, at the MGM Grand Garden in Las Vegas was his first appearance in the UFC since 1996. He met Tito Ortiz, who had become the light heavyweight champion and one of the faces of the promotion, in the night’s main event.

Shamrock had gone into the WWE and was dubbed “The World’s Most Dangerous Man” in his time there. But at UFC 40, Ortiz proved to be the world’s most dangerous fighter.

Ortiz won by TKO when Shamrock’s corner threw in the towel after three rounds. Referee John McCarthy said afterward that was the first time he felt MMA was going to make it, judging by the size and the passion of the crowd.

16. BMF title introduced at Madison Square Garden as President Trump watches cageside

After a win over former lightweight champion Anthony Pettis at UFC 241, Nate Diaz looked out toward the audience at the Honda Center in Anaheim, California, and called out Jorge Masvidal.

Little did they know it, but the birth of a new title was born. Diaz and Masvidal met for the so-called BMF title at UFC 244 on Nov. 2. BMF stands for “Baddest Mother F***er” and the UFC made a belt for it.

It made the fight as the main event at Madison Square Garden in New York, had the actor Dwayne “The Rock” Johnson put the belt on the winner and was the first UFC event in which a sitting American president watched from cageside. President Donald Trump was in the crowd of 20,143 as Masvidal stopped Diaz on cuts after three rounds.

It was supposed to be a one-time thing, but fighters and fans embraced it. Justin Gaethje and Dustin Poirier would fight for the BMF belt a second time on July 29 at UFC 291 in Salt Lake City. That bout was one of the three best-selling of 2023 to this point.

15. Zuffa acquires UFC from SEG for $2 million in 2001

In what turned out to be the best deal since the Louisiana Purchase, brothers Frank and Lorenzo Fertitta and partner Dana White purchased the UFC from Semaphore Entertainment Group for $2 million. White was installed as president.

Though there were positive signs before the sale, the deal wasn’t a guaranteed success for the Fertittas, who named the company Zuffa. Unified rules had just been passed, and the sport had just gotten back onto cable television after a ban.

But the Fertittas’ business expertise helped drive the company up and despite being in a $40 million hole early, they broke out of it after airing “The Ultimate Fighter” in 2005. It ultimately became a massive worldwide success.

14. Royce Gracie wins UFC 1 tournament

The UFC debuted on Nov. 12, 1993, at McNichols Arena in Denver, a venue chosen specifically because the state didn’t have an athletic commission at the time that would regulate the event. It ostensibly was designed to decide which fighting style was best.

There were no weight classes and fighters ranged in size from Royce Gracie’s 180 pounds to Teilia Tuli’s 450 pounds. Gracie defeated a boxer, Art Jimmerson, who wore only one glove in the fight, with a smother choke. Tuli faced the 204-pound Gerard Gordeau, who won in the first round in 26 seconds when he kicked Tuli in the face and knocked several teeth out. Two of the teeth remained embedded in Gordeau’s foot.

But Gracie, by far the smallest man in the eight-man field, submitted Ken Shamrock and Gordeau in the next two rounds via rear naked choke. And with that, UFC 1 was off and running and Brazilian Jiu-Jitsu became a thing in the U.S.

13. Forrest Griffin-Stephan Bonnar save UFC at TUF Finale 1

More than $40 million in debt and looking to sell the company, the Zuffa owners put together a reality series, “The Ultimate Fighter,” in a desperate and last-ditch attempt to popularize and teach MMA to the masses.

The final show of the season was televised live April 4, 2005, on Spike TV from a basketball practice gym, the Cox Pavilion, on the UNLV campus. It became the first MMA show broadcast live and free on cable TV in the U.S. The final bout featured Stephan Bonnar versus Forrest Griffin.

It was an amazing slugfest that had the crowd on its feet, roaring, throughout. People were calling friends and telling them to turn the fight on.

After it was over, and Griffin won, executives from Spike and Zuffa met in the parking lot and hammered out an extension for a Season 2. Without that bout, MMA may have ceased to exist.

12. Nate Diaz: 'I’m not surprised, mother f***ers'

UFC 196 was held on March 5, 2016, at the MGM Grand Garden and was supposed to feature featherweight champion Conor McGregor moving up to lightweight to challenge champion Rafael dos Anjos. Dos Anjos was injured and had to withdraw, and several fighters, notably Frankie Edgar and Jose Aldo, weren’t available to take the fight on short notice.

Eventually, the UFC settled on former TUF winner Nate Diaz as McGregor’s opponent. The trash talk in the short build-up was wild, but McGregor was favored.

McGregor had his moments in the bout, but he started to tire in the second and Diaz started to take over. He caught McGregor in a rear naked choke and forced McGregor to tap at 4:09 of the second round. That started one of the UFC’s great rivalries.

Interviewed in the cage by Joe Rogan afterward, a nonchalant Diaz said dryly, “I’m not surprised, mother f***ers.”

11. Jon Jones becomes youngest UFC champion at UFC 128

Mauricio “Shogun” Rua was supposed to defend his belt on March 19, 2011, at the Prudential Center in Newark, New Jersey, against former champ Rashad Evans. Evans was injured and the UFC gave the bout to Jon Jones.

Jones put on an awesome display of fighting and won the title at 23 years, 8 months and 1 day old, stopping Rua at 2:37 of the third round. He became the youngest champion in UFC history, a record that stands to this day.

10. Anderson Silva survives grave threat, retains title late

Chael Sonnen started trash talking Anderson Silva long before the two ever signed to fight for Silva’s middleweight title at UFC 117 on Aug. 7, 2010, in Oakland, California. He ratcheted the talk up several notches when the fight was official and threatened to pummel Silva, who by that point was regarded as the greatest fighter in MMA history.

When the bell sounded, incredibly, Sonnen was doing what he said. For four rounds, he dominated Silva in a one-sided bout. He was doing so for a while in the fifth, but Silva managed to catch him in a triangle choke and forced him to tap at 3:10 of the final round.

It was one of the most dramatic fights in UFC history and cemented Silva’s legend.

9. Anderson Silva loses title to Chris Weidman

Anderson Silva had won 17 fights in a row, 16 of them in the UFC and 12 of them wins in middleweight title bouts, when he signed to fight Chris Weidman at UFC 162 on July 6, 2013, in Las Vegas.

Silva was showboating as he was trying to open Weidman so that he could counter punch him. But Weidman caught Silva with his hands down and knocked him out, ending his long title streak.

In the rematch that December, a leg kick grotesquely snapped Silva’s leg.

8. Women debut at UFC 157

Dana White had famously said he’d never have women fight in the UFC, and for more than 12 years of his ownership, he stuck to that. But then he met Ronda Rousey and things changed.

At UFC 157 at the Honda Center in Anaheim, California, on Feb. 23, 2013, women’s bantamweight champion Ronda Rousey defended her title against Liz Carmouche. Rousey had won the title in Strikeforce and just kept it when she was brought into the UFC.

Rousey and Carmouche fought in the main event of the card, further emphasizing the point that women were finally being treated equally to the men. Rousey won by armbar submission at 4:49 of the first round.

7. Wild brawl erupts following UFC 229

Khabib Nurmagomedov defended his lightweight title against Conor McGregor on Oct. 6, 2018, at T-Mobile Arena in what would become the greatest-selling pay-per-view card in UFC history. It did more than 2.4 million buys.

But a dark and ugly build-up turned into a nightmare for the UFC following the main event, which Nurmagomedov won by fourth-round submission.

After releasing the hold on McGregor, Nurmagomedov leaped the cage to go after Dillon Danis, one of McGregor’s cornermen who had been taunting him. That precipitated a wild brawl that was on both the outside and inside of the Octagon. Nurmagomedov and McGregor, as well as others, were suspended by the Nevada Athletic Commission for their roles in the incident.

6. Rousey stunned by Holm in massive upset

By the time she was set to face Holly Holm at Docklands Stadium in Melbourne, Australia, at UFC 193, Rousey had become a cultural icon. She was 12-0 with 12 finishes, 11 of which came in the first round. She’d finished her three previous fights in a combined total of 64 seconds.

She was starring in movies and making the rounds on the late-night talk show circuit.

But she was not the same fighter against Holm, a future Hall of Fame boxer who dominated her from start to finish. Rousey was stopped by a kick to the head at 59 seconds of the first round in what remains to this day the biggest upset in UFC history.

5. McGregor psychs out Aldo, wins title in a flash

Conor McGregor absolutely tormented Jose Aldo during a worldwide media tour for their bout that was set for Dec. 12, 2015, in the main event of UFC 194 in Las Vegas. At a news conference in Dublin, Aldo attempted to attack McGregor but was restrained.

When the bell rang, Aldo stormed out of the corner to attack McGregor, as McGregor surmised. McGregor sidestepped a huge punch and landed a crushing counter left hook that put Aldo out just 13 seconds into the bout.

4. MMA legalized in New York

On April 14, 2016, New York Gov. Andrew Cuomo signed a bill that legalized mixed martial arts in the state, ending a ban that had been in effect for nearly 20 years. As other states were being legalized, New York was the obvious one that the UFC wanted to open.

Ratner, his staff, UFC officials and prominent fighters made numerous treks to New York to meet with politicians in a bid to legalize the sport. On March 22, the state assembly passed a bill that did that, and Cuomo pledged to sign it.

It was a huge day for all MMA promoters, but particularly the UFC, which quickly announced plans to hold a series of fights in not only New York but throughout New York State.

3. McGregor-Diaz rematch a memorable fight

Conor McGregor and Nate Diaz agreed to rematch at UFC 202 on Aug. 20, 2016 at T-Mobile Arena in Las Vegas. The pre-fight news conference was notable because McGregor was extremely late. As McGregor finally arrived, Diaz and his team were irritated and left.

The fight was a classic and McGregor used his striking to get out to an early lead. As he tired, Diaz came on and the fight was very close. McGregor won a majority decision in a tremendous bout that left the audience in awe.

2. Conor McGregor becomes first double champion

Just three months after avenging his loss to Nate Diaz, Conor McGregor announced he was going to try to win the lightweight title by facing champion Eddie Alvarez at UFC 205 on Nov. 12, 2016, in New York. While there had been fighters who had won two titles in multiple divisions in the UFC, to that point, no one held two weight-class belts simultaneously.

In what might have been peak McGregor, he easily picked apart Alvarez and stopped him at 3:04 of the second round. Since McGregor did it, Daniel Cormier (light heavyweight, heavyweight), Amanda Nunes (bantamweight, featherweight) and Henry Cejudo (flyweight, bantamweight) have accomplished it.

1. Endeavor purchases UFC for $4 billion

For much of the spring and summer of 2016, rumors swirled that the UFC was for sale. The day after its seminal event, UFC 200, news broke that Endeavor had purchased controlling interest in the UFC for a staggering $4.025 billion. In 2021, Endeavor purchased the remainder of the company and now owns a 100 percent interest.

The sale was credited with allowing the UFC to take the final, most difficult steps by reaching the American mainstream. Led by Ari Emanuel, who is a noted expert at media deals, the UFC left Fox and landed a broadcast deal with ESPN. The company was also able to attract more sponsors and at a higher level. Anheuser-Busch recently did a deal worth in excess of $100 million for a Bud Light sponsorship with the UFC.

The deal wasn’t as exciting for fans as the great fights that took place under Endeavor’s leadership, but it put the UFC into a more solid financial footing and made the company a major player in the sporting world.