The 10 Biggest Fights in UFC History

The Ultimate Fighting Championship’s marketing machine, which is second to none in the mixed martial arts industry, is always pushing the next high profile matchup as the “biggest fight ever.”

With the impending blockbuster of an event in UFC 100 slated to kickoff on July 11 from Mandalay Bay in Las Vegas, Nevada it is important to examine the how we arrived at this historic event and past fights that have been landmarks leading us up to UFC 100 and beyond.

Quality fights make quality events, but the most important fights in the history of the UFC are not necessarily the most exciting nor do they all have highlight reel finishes.

What they do all have in common is a broad importance to the current state of the UFC and the sport of MMA in general.

They are significant historical milestones that have marked the rise of the UFC, fighters coming back from retirement, intense rivalries, and pay-per-view blockbusters.  This list has a little bit of everything.

Without further ado, these are the ten biggest fights in the history of the UFC in chronological order.

UFC 5 – Royce Gracie vs. Ken Shamrock 2
April 7, 1995 – Charlotte, NC – Independence Arena
Result: Draw – Round 1 – 36:00

This battle between UFC immortals and future hall-of-famers was the second matchup between these superstars.

Entering their first meeting at UFC 1 they were virtual unknowns but by the time UFC 5 rolled around they were two of the premier figureheads of “no rules” fighting.

This “superfight championship” was a grueling test of endurance and was eventually declared a draw after thirty six minutes because there were no judges.

It remains the longest fight in the history of the UFC.

UFC 40 – Tito Ortiz vs. Ken Shamrock
November 22, 2002 – Las Vegas, NV – MGM Grand
Result: TKO victory by Ortiz – Round 3 – 5:00

Shamrock made his return to the UFC since 1996 to battle current light heavyweight champion Tito Ortiz in what would be the first of three meetings between these two hated rivals.

Ortiz had successfully defended his belt four times coming into this matchup and his victory over Shamrock would be an impressive fifth, however, “The Huntington Beach Bad Boy” would never win a title fight ever again.

He lost to Randy Couture at UFC 44 in his next fight and to Chuck Liddell at UFC 66.

UFC 46 – Matt Hughes vs. B.J. Penn
January 31, 2004 – Las Vegas, NV – Mandalay Bay
Result: Submission victory by Penn – Round 1 – 4:39

Penn stopped the longtime welterweight champion Hughes’ six fight UFC win streak in a stunning upset.

After eight career fights at the lightweight level Penn jumped up in weight to challenge Hughes and he more than held his own sinking in a rear naked choke in the first round.

After his victory over Hughes, Penn vacated his belt due to his lack of challenging fights left for him in the UFC.  He signed with the Japanese promotion FEG and would not be seen in the UFC again until two years later in 2006.

Penn would have to wait all the way until UFC 80 to win a lightweight championship belt and to become the second fighter in UFC history to win championships in two separate weight classes.

UFC 52 – Chuck Liddell vs. Randy Couture 2
April 16, 2005 – Las Vegas, NV – MGM Grand
Result: KO victory by Liddell – Round 1 – 2:06

The first matchup between these two legendary warriors resulted in a surprising knockout victory by Couture who essentially outpunched the puncher Liddell.

The rematch between two of the brightest stars in MMA history was much anticipated.  With a devastating first round knockout by Liddell he instantly turned from star to superstar.

It would turn out to be the catalyst he needed to start a dominant run through the UFC’s premier division over the course of the next two years.

He would also take the UFC and the sport of MMA to new heights along the way.

Ultimate Fighter 1 Finale – Forrest Griffin vs. Stephan Bonnar 1
April 9, 2005 – Las Vegas, NV – Cox Pavilion
Result: Griffin via unanimous decision – Round 3 – 5:00

There might not be a UFC today if this fight had not taken place. This is the fight that is credited with turning thousands of MMA newcomers into fans, and at the same time, turning many more fair-weathered fans into hardcore fans.

Everyone loves a slugfest and this fight did not disappoint. For three rounds Griffin and Bonner went toe-to-toe landing shot after shot on one another but there was no quit on either side. Each guy refused to back down until the final horn.

When it was all said and done it would be the spark the UFC needed to turn a business that was millions of dollars in debt headed in the opposite direction.

UFC 60 – Matt Hughes vs. Royce Gracie
May 27, 2006 – Los Angeles, CA – Staples Center
Result: TKO victory by Hughes – Round 1 – 4:39

It was the return of legend Royce Gracie after an eleven year absence in the UFC. This time he was pitted against the long-time dominant welterweight champion Matt Hughes at a catch-weight of 175 pounds.

It was old school vs. new school and a changing of the guard in the evolution of the sport.
No longer would a one dimensional fighter like Gracie be effective in the UFC.

The sport had begun to pass him by at that point in time and only well-rounded fighters like Hughes would rule the UFC going forward.

The Hall-of-Famer Gracie would never fight in the UFC again.

UFC 66 – Chuck Liddell vs. Tito Ortiz 2
December 30, 2006 – Las Vegas, NV – MGM Grand
Result: TKO victory by Liddell – Round 3 – 3:59

The second leg of this historic rivalry to this day remains the highest grossing live gate in the history of the UFC with just under $5.4 million in gross revenue.

There was big demand for a rematch of their UFC 47 bout that was won by Liddell due to their high profiles as growing celebrities and their long standing feud with one another.

Liddell would score a devastating knockout victory that would leave Ortiz bloodied on the canvas.

It would be the last time that Liddell would exit the UFC octagon as a champion.

UFC 68 – Randy Couture vs. Tim Sylvia
March 3, 2007 – Columbus, Ohio – Nationwide Arena
Result: Couture via unanimous decision – Round 5 – 5:00

This fight marked the return of Randy Couture out of retirement at the age of 44. Nobody had any clue what to expect out of Couture coming into this fight. He had not fought in over a year since losing to Chuck Liddell at UFC 57.

With an overhand right to the chin of Sylvia just after the fight began the tone was set for the duration of the bout. Couture was able to control Sylvia for the better part of five rounds with his hands and his wrestling and secure yet another championship belt for the trophy case.

It would be a rebirth for Couture and the start of a career downfall for Sylvia, who would lose three of his next four MMA fights.

UFC 91 – Randy Couture vs. Brock Lesnar
November 15, 2008 – Las Vegas, NV – MGM Grand
Result: TKO victory by Lesnar – Round 2 – 3:07

It was an old school vs. new school heavyweight battle that had all the makings leading up to the fight.

Lesnar was 1 – 1 in the UFC and was controversially granted a shot at the title against the veteran Couture mainly because of his ability to draw a pay-per-view audience.

He his Couture with a series of hammer fists that prompted the referee to call off the fight and many questions were answered about the authenticity of Lesnar’s ability and talent as an MMA fighter.

UFC 94 – Georges St. Pierre vs. B.J. Penn
January 31, 2009 – Las Vegas, NV – MGM Grand
Result: TKO victory by St. Pierre – Round 4 – 5:00

This matchup was arguably the most hyped UFC fight of all-time.

The UFC management pulled out all the stops promoting this event by launching a UFC Countdown show leading up to the fight.

Not very often do two of the consensus top five pound-for-pound fighters in the world do battle and this was a rare treat for MMA fans.

It was the current UFC welterweight champion St. Pierre versus the current UFC lightweight champion Penn.

It was also marketed as good vs. evil and the buzz surrounding this fight was so palpable it was almost certain to disappoint on fight night.

That was the case as St. Pierre used his dominant size and strength to control the fight early and often and secure a rather boring victory.

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