The 5 Most Shocking Upsets In MMA History

Much has been said about mixed martial arts (MMA) over the years — it’s epic displays of skill and determination, and marvelous stories of triumph and defeat. Fans have been witness to some of the most compelling bouts over the past two decades. Today, MMA is one of the most popular sports in the world, enjoyed by millions of fans.

Just as in all sports, there are winners and there are losers — favorites and underdogs. Sometimes, however, those who are supposed to win actually wind up losing. When the favorite of a match loses, and the underdog wins, this is called an ‘upset’.

Upsets in MMA are absolutely shocking because they come when you least expect it. When upsets happen, they usually produce a collective dropping of jaws on the floor. Needless to say, they come completely out of left field.

The great warriors of the cage spend so much time preparing for their bouts that it’s kind of tough to deal with the realization that there can only be one winner. This has happened on multiple occasions throughout the sport’s history.

It’s time to revisit some of the most surprising instances when things didn’t go exactly as expected. Today, Evolve Daily shares the five most shocking upsets in MMA history.

1) Matt Serra Vs Georges St. Pierre, UFC 69

After emerging as the winner of the fourth season of The Ultimate Fighter, UFC welterweight Matt Serra earned himself a $100,000 UFC contract and a shot at the UFC welterweight title then held by Canadian Georges St. Pierre (GSP).

GSP is, of course, one of the all-time greats in MMA. His pedigree is legendary and has defeated some of the biggest names in the sport. On the other side of the spectrum, Serra had no business being in the Octagon with GSP and was expectedly the underdog going into the matchup.

Many fans predicted that GSP would go on to completely obliterate Serra, who was a solid fighter in his own right, but certainly not on the same level of the champ. What happened at UFC 69 would go down as one of the greatest upsets in the history of the sport.

Not only did Serra beat GSP, he utterly destroyed him, finishing via first-round technical knockout. Though GSP would exact revenge against Serra in the rematch, no one can erase what happened. It is GSP’s first and only loss by knockout.


2) BJ Penn Vs Matt Hughes, UFC 46

Before “The Prodigy” BJ Penn met legend Matt Hughes at UFC 46, he had already made a name for himself in the UFC’s lightweight division. After the promotion disbanded the weight class in 2003 however, the remaining lightweights had no choice but to move up to welterweight. Penn was considered by many to be too small to compete at welterweight.

In his first fight in his new division, Penn drew a shot at the UFC welterweight title. Fans obviously believed Hughes would end up being too big and too strong for Penn, and for good reason. But what transpired that evening really stamped Penn’s legacy, and his submission win over Hughes would go down in history as one of the most shocking upsets in the UFC. 

Late in the first round, Penn staggered Hughes with a big punch that sent the champion reeling. The Hawaiian then took Hughes’ back and finished him with a rear naked choke.


3) Fabricio Werdum Vs Fedor Emelianenko, Strikeforce

When you talk about MMA legends, there is none bigger than “The Last Emperor” Fedor Emelianenko. The Russian heavyweight is arguably and widely considered the greatest of all time in MMA. His combination of strength, skill, and sheer dominance is unparalleled.

In 2010, Emelianenko would meet Brazilian Fabricio Werdum. At the time, Emelianenko had just one loss on his record and was riding an incredible 28-fight win streak. Fans believed there was no way that streak was going to end. It was just inconceivable. But Werdum, a seasoned grappler, knew he had the advantage on the mat.

Werdum survived Emelianenko’s early onslaught and later lured the Russian to the ground and into his guard. It was then that Werdum latched onto a triangle armbar that had Emelianenko tapping out for the first time in his career. It was a pure Brazilian Jiu-Jitsu effort as Werdum did not land a single strike in that final round.


4) Nate Diaz Vs Conor McGregor, UFC 196

“The Notorious” Conor McGregor is arguably MMA’s biggest star right now, and his remarkable run through the ranks over the past few years has been nothing short of epic. McGregor has absolutely torn through the opposition since he made his UFC debut in 2013 with a technical knockout over Marcus Brimage.

After winning the featherweight title with a 13-second KO of Jose Aldo, McGregor had his eyes set on the lightweight strap, then held by Rafael Dos Anjos. No one, it seemed, would be able to derail the McGregor hype train.

When Dos Anjos had to pull out from the fight, however, it was Nate Diaz who stepped in on just 11 days’ notice. On vacation at the time, Diaz was out of shape and nowhere near the lightweight limit. He had instead negotiated for the fight to be at welterweight.

With absolutely no training and just a couple of days removed from sipping pina coladas on the beaches of Mexico, Diaz stepped into the Octagon with the UFC’s biggest spectacle. Diaz ended up authoring one of the most incredible upsets in MMA history, finishing McGregor with a rear-naked choke in the second round.


5) Royce Gracie Vs Everybody, UFC 1

There have been a lot of UFC legends over the last two decades, but none bigger than the man himself, Royce Gracie. Gracie was part of the first-ever UFC event and compared to the other guys competing, he looked soft at 170-pounds. No one was intimidated at all by what Gracie brought to the table — big mistake. 

Brazilian Jiu-Jitsu had its big introduction to the martial arts world on that night, as Gracie defeated all of his opponents with astute grappling to bag the whole tournament. Through BJJ, Gracie proved that a small man can beat a big man with sound technique. Gracie blitzed through legends Art Jimmerson, Ken Shamrock, and Gerard Gordeau to win UFC 1. 

Most impressively of all, Gracie made it look easy. He was the originator, the pioneer of the sport we love, even before it became known as MMA. Today, BJJ is one of the most popular martial arts in the world and is one of the foundations of mixed martial arts.

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