Biggest Boxing PPV fights of the last 20 years - Combat Sport Events

Biggest Boxing PPV fights of the last 20 years

Since the pay-per-view’s (PPV) inception and introduction to boxing in 1948, the word has become synonymous with the biggest fights the sport has to make. Over the past 20 years, the world has seen some of the most incredible fights propelling boxing to new heights. While the Heavyweight division began to decline and suffered in PPV buys other divisions soared catapulting fighters like Manny Pacquiao and Floyd Mayweather JR to superstardom and creating some of the biggest fights of all time.

In this article, I will review and breakdown just exactly what was the biggest PPV fights over the last 20 years. Year by year which fight came out on top and at the end which ultimately sold the most Pay per views.


Oscar De La Hoya vs. Shane Mosley

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The decade kicked off with a phenomenal fight between two icons. One of the most popular fighters and ranked as one the greatest boxers of all time the Golden Boy Oscar De La Hoya took on Sugar Shane Mosley who was coming off 2 loses and 1 no contest.

Mosley took the win handing De La Hoya the second loss of his career at that point.

De La Hoya generated approximately $700 million in pay-per-view income and was leading as the PPV King before becoming ultimately surpassed by Floyd ‘Money’ Mayweather.


Naseem Hamed vs. Marco Antonio Barrera

The flamboyant and charismatic ‘Prince’ Naseem Hamed travelled to Las Vegas Nevada to take on the tough Mexican opponent Marco Antonio Barrera. Barrera handed Naseem his first and only loss claiming the lineal featherweight championship. 

Barrera, unfazed by the unorthodox fighting style of Naseem, boxed his way to a unanimous decision. An excellent fight to watch with moments of magic mixed with moments of scrappy behaviour between the two fighters.


Mike Tyson vs. Lennox Lewis

A ferocious fight fuelled by emotion, Mike Tyson vs Lennox Lewis battled it out for the heavyweight lineal crown in the year 2002.

Tyson was declining after his spell in prison and Lewis was at the pinnacle of his career. The fight between these 2 icons went on to become the highest-grossing event in pay-per-view history at that time with a whopping 1.95 million buys in the US alone.


Oscar De La Hoya vs. Shane Mosley II

Following the big success of the previous fight Oscar De La Hoya and Shane Mosley squared off for the second time. If this fight was anywhere near as good as the first it would be a great fight.

The fight was entertaining and exciting but ultimately left fans frowning once again at judges decision making as the result was a unanimous decision but very controversial.


Bernard Hopkins vs. Oscar de la Hoya

A strategic battle between the 2 legends took place in Las Vegas, Nevada. After losing to Shane Mosley in a phenomenal fight the ‘Golden Boy’ Oscar De La Hoya jumped up weight to face undisputed middleweight champion Bernard Hopkins in a tactical battle.

Hopkins would ultimately win by handing the Mexican-American his first loss via Knockout.


Antonio Tarver vs Roy Jones Jr. III

A tight split decision win for Roy Jones and a knockout for Tarver left fans wanting more. Entering the rubber match with 1 win apiece over each other tensions were high. 

This fight had everything. From Tarver almost falling over the ropes to a perfect classic Roy Jones display of boxing in round number 5. Such drama throughout the fight it’s well worth a watch.


Ricardo Mayorga vs. Oscar de la Hoya

In a fight just prior to his bout with Floyd Mayweather de la Hoya knocked out Ricardo Mayorga who at the time was for the WBC light middleweight title. De la Hoya came out with the TKO victory in this one-sided beatdown crowning him WBC middleweight champion.


Oscar de la Hoya vs. Floyd Mayweather Jr

In a fight dubbed as ‘The World Awaits’ Floyd ‘Money’ Mayweather took on The ‘Golden Boy’ Oscar de la Hoya in a fight that would see Floyd box out a split decision. Oscar De La Hoya ended up earning $52 million and the PPV numbers reached 2.4 million buys.


Oscar de la Hoya vs. Manny Pacquiao

A rare sight in this fight when de la Hoya refused to fight on against Pacman. This fight demonstrated the timing, precision and speed of Pacquiao catapulting him into boxing superstardom. A win against one of the greatest fighters of all time etched Manny’s name in history and will go down as one of his best performances.


Floyd Mayweather Jr vs. Juan Manuel Márquez

In Floyd’s 40th fight he took on the legend that is Juan Manuel Márquez who was 50-4 at the time in superfight for the ages. Winning a unanimous decision Floyd came out with the W after his 2-year layoff.


Floyd Mayweather Jr vs. Shane Mosley

In a fight between two giants of the sport, Mayweather beat Mosley to go 41-0 as a pro. The fight opened up with a hard right from Mosley that seemed to stun Floyd who held on for dear life. After overcoming an early onslaught Mayweather remained calm and was able to point his way to a unanimous decision. A great fight between the two fighters brought in 1.4 million PPV buys.


Manny Pacquiao vs. Juan Manuel Márquez III

3 times a charm. They say that styles make fights and this fight was no exception. With a draw during the first fight and a narrow win for Pacquiao in the second fight, the stakes were high coming into the third fight. Pacquiao ultimately pulled off the victory edging out Juan Manuel Márquez on the scorecards.


Floyd Mayweather Jr vs. Miguel Cotto

A tough battle for both fighters in prediction, however, it turned out to be a clear victory for Floyd. A competitive battle, all the same, it’s a great watch and demonstrates the two fighters heart and ability.


Floyd Mayweather Jr vs. Canelo Álvarez

The only blemish on an otherwise perfect career of Canelo Álvarez’s career is the loss to Floyd Mayweather. Outclassed by the seasoned vet Canelo’s first and only loss was to a defensive genius that is Floyd Mayweather. In my opinion, the Canelo we know now is a different beast to the on that fought Floyd in 2013 and if they were to fight again it would be a different outcome.


Floyd Mayweather Jr vs. Marcos Maidana II

After an exciting first fight between the two fighters, many were surprised that Mayweather would take another fight against the hard-hitting Marcos Maidana. Although not as exciting as the first fight, in my opinion, it is still a great fight nonetheless.


Floyd Mayweather Jr vs. Manny Pacquiao

The battle of the century. The two powerhouses of boxing collide in a boxing match years in the making. An event that captured the interest of casual fans and hardcore boxing fans alike it was considered a let down by fans and critics however it tops the poll of all-time PPV buys.


Canelo Álvarez vs. Amir Khan

A fight displaying a devastating knockout that tops Canelos’s sensational highlight reel. This fight lived up to the hype showcasing Amir Khan’s lightning-fast speed and Canelo’s accuracy and strength.


Floyd Mayweather Jr vs. Conor McGregor

Titled ‘The Money Fight’ the battle of combat sports collided when UFC star Connor McGregor stepped inside the squared circle to face one of the greatest boxers of all time.

The 0-0 fighter took on the 49-0 veteran in a fight that grossed over 5.4 million PPV buys and was the 2nd highest-grossing boxing fight of all time.


Anthony Joshua vs. Joseph Parker

AJ’s boxing ability shone through with his title win over Kiwi Joseph Parker in what was his biggest test to date. Parker is possibly one of the most skilled boxers in the heavyweight division with a previous win over Andy Ruiz.


Andy Ruiz Jr. vs. Anthony Joshua II

Following the biggest upset since Tyson vs Douglas, the rematch between AJ and Ruiz was highly anticipated. The drama began when Joshua weighed in much lighter and Ruiz weighed in 15lbs heavier than the first fight. Although not as explosive and dramatic as the first bout the rematch showed AJ’s incredible Boxing ability.


Deontay Wilder vs. Tyson Fury II

The highly anticipated rematch between the heavyweight giants Tyson Fury and Deontay Wilder ended in spectacular fashion with Fury stopping Wilder in round 7. An outcome that frankly nobody saw coming apart from Tyson himself and his team.

An absolute classic matchup that leaves us in great anticipation for the rubber match.

So far in the year 2020, this remains on top, however, with several massive fights set to take place throughout the year, it will be hard to keep this top spot.

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