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ARLINGTON, TX - MARCH 13:  Manny Pacquiao of the Philippines celebrates in the ring after defeating Joshua Clottey of Ghana during the WBO welterweight title fight at Cowboys Stadium on March 13, 2010 in Arlington, Texas. Pacquiao defeated Clottey by unan
ARLINGTON, TX - MARCH 13: Manny Pacquiao of the Philippines celebrates in the ring after defeating Joshua Clottey of Ghana during the WBO welterweight title fight at Cowboys Stadium on March 13, 2010 in Arlington, Texas. Pacquiao defeated Clottey by unanTom Pennington/Getty Images

Punching With Pac-Man: Manny Pacquiao's 10 Toughest Fights

Michael TerrenceNov 8, 2010

For the past fifteen years, Manny Pacquiao has obliterated nearly every opponent put in front of him. This weekend he will attempt to capture a title in a record eighth weight class. Pacquiao is a heavy favorite over Mexico’s Antonio Margarito.

The 5 ft 5 ½ in Pacquiao has made a career out of defying the odds and going up in weight to take out bigger and stronger men. In his 56 professional fights, only 18 of them have gone the distance. He has won 7 of his last 10 fights by stoppage. The only three fighters to go the distance were; Oscar Larios, Juan Manuel Márquez and Marco Antonio Barrera.

It’s worth mentioning that the latter spent much of the fight in full retreat to avoid being knocked out.

Simply put, the Filipino warrior is one of the best pugilist’s of All-Time. He was named Fighter of the Decade for the 2000’s and could probably fight as high as Middleweight and still be a dominant force.

As accomplished as Pacquiao is there were a few foes he gave him all he could handle and in some cases, more than he could handle.

So here are the 10 toughest fights of Manny Pacquiao’s career.

10. Oscar De La Hoya

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LAS VEGAS - DECEMBER 06:  Manny Pacquiao (R) hits Oscar De La Hoya in the fifth round of their welterweight bout at the MGM Grand Garden Arena December 6, 2008 in Las Vegas, Nevada.  (Photo by Ethan Miller/Getty Images)
LAS VEGAS - DECEMBER 06: Manny Pacquiao (R) hits Oscar De La Hoya in the fifth round of their welterweight bout at the MGM Grand Garden Arena December 6, 2008 in Las Vegas, Nevada. (Photo by Ethan Miller/Getty Images)

Now before you close this post and disregard it as foolish, hear me out.

 On paper this fight was supposed to be tremendously one-sided. It was setup for De La Hoya to finish his career on top by beating a quality, big name opponent. The fight was even titled “The Dream Match.”

In reality it was a sham. De La Hoya who made a living as one of the top welterweights for many years, was forcing Pacquiao to jump up two weights and fight in a class he’d never fought in before. A task that many boxing experts believed was too big and thus heavily criticized De La Hoya for picking on a smaller man.

The fight did indeed turnout to be a one-sided affair. Unfortunately for the “Golden Boy,” he was on the wrong side. For eight rounds Pacquiao stalked, battered and befuddled an overmatched De La Hoya. The fight got so bad that at one point, Manny had Oscar pinned in a corner and De La Hoya was holding onto the ropes to keep from being knocked down.

After eight rounds, De La Hoya’s corner mercifully stopped the massacre. De La Hoya marched over to Pacquiao congratulated him and told his former trainer Freddie Roach that his observation was correct, when he insisted prior to the bout that “De La Hoya was a shot fighter.”   

9. Jorge Solis

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SAN ANTONIO - APRIL 14:  Manny Pacquiao of the Philippines (L) in action against Jorge Solis of Mexico during the WBC International Featherweight Championship April 14, 2007 at the Alamodome in San Antonio, Texas.  (Photo by Jed Jacobsohn/Getty Images)
SAN ANTONIO - APRIL 14: Manny Pacquiao of the Philippines (L) in action against Jorge Solis of Mexico during the WBC International Featherweight Championship April 14, 2007 at the Alamodome in San Antonio, Texas. (Photo by Jed Jacobsohn/Getty Images)

Despite being undefeated, Jorge Solis was a lightly regarded Super-Featherweight contender when he stepped into the ring with Pacquiao.  

In Fact, Solis was only given the title fight after negotiations failed for a Pacquiao and Marco Antonio Barrera bout.

The fight took place April 14, 2007 in San Antonio, Texas. Solis was tougher than anyone expected and provided a real test for Manny in the early rounds. The fight took an interesting turn when Pacquiao was cut by a clash of heads in the sixth round.

Ever the champion, Pacquiao battled through the blood and dropped Solis to the canvas in the eighth round. Solis was able to recover but was again floored later in the same round. The referee stepped in giving Pacquiao the 44th victory of his career.  

8. Agapito Sánchez

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ARLINGTON, TX - MARCH 13:  Manny Pacquiao of the Philippines looks on in the ring against Joshua Clottey of Ghana during the WBO welterweight title fight at Cowboys Stadium on March 13, 2010 in Arlington, Texas. Pacquiao defeated Clottey by unanimous deci
ARLINGTON, TX - MARCH 13: Manny Pacquiao of the Philippines looks on in the ring against Joshua Clottey of Ghana during the WBO welterweight title fight at Cowboys Stadium on March 13, 2010 in Arlington, Texas. Pacquiao defeated Clottey by unanimous deci

Agapito Sánchez should probably have been disqualified for his antics in the ring that night. He was deducted two points for throwing low blows. The bout was stopped at one point in the fourth round to allow Pacquiao time to recover from a Sanchez foul.

Yet, despite the numerous fouls, Sanchez was a game opponent and controlled the early rounds of the fight. Pacquiao was fighting an uphill battle from early on in the fight; he took the worst end of an accidental head butt and suffered a cut above his right eye in the 2nd round.

Pacquiao wasn’t deterred and fought on valiantly and appeared to be gaining the upper hand in spite of the fouls Sanchez was committing.

The bout was halted in the sixth round when the ringside doctor stopped the fight because of the severity of the cut above Pacquiao’s eye. The three ringside judges scored the fight; 55-57 (Sanchez), 58-54 (Pacquiao), and 56-56.

The fight was declared a draw and both men retained their titles.

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7. Medgoen Singsurat

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ARLINGTON, TX - MARCH 13:  Manny Pacquiao of the Philippines looks on in the ring after defeating Joshua Clottey of Ghana during the WBO welterweight title fight at Cowboys Stadium on March 13, 2010 in Arlington, Texas. Pacquiao defeated Clottey by unanim
ARLINGTON, TX - MARCH 13: Manny Pacquiao of the Philippines looks on in the ring after defeating Joshua Clottey of Ghana during the WBO welterweight title fight at Cowboys Stadium on March 13, 2010 in Arlington, Texas. Pacquiao defeated Clottey by unanim

Manny Pacquiao was the Flyweight champion and was coming off of a 4th round knockout victory in his first title defense. It probably should have been his last fight at 112 pounds. Pacquiao’s body was naturally growing and he could not make the weight anymore.

In his second title defense he fought Medgoen Singsurat. Singsurat is far from a household name. Even Bert Sugar might struggle if asked to name another big fight Singsurat was in besides his one with Pacquiao.

Pacquiao was overweight at the weigh-in and completely drained by fight time. Singsurat crushed Pacquiao with a body shot in the 3rd round and he was unable to get up.

The loss to Singsurat was the 2nd loss of Pacquiao’s career. The bout was Pacquiao’s last at that weight.   

6. Rustico Torrecampo

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LAS VEGAS - NOVEMBER 14:  (L-R) Miguel Cotto of Puerto Rico throws a left to the head of Manny Pacquiao during their WBO welterweight title fight at the MGM Grand Garden Arena on November 14, 2009 in Las Vegas, Nevada.  (Photo by Al Bello/Getty Images)
LAS VEGAS - NOVEMBER 14: (L-R) Miguel Cotto of Puerto Rico throws a left to the head of Manny Pacquiao during their WBO welterweight title fight at the MGM Grand Garden Arena on November 14, 2009 in Las Vegas, Nevada. (Photo by Al Bello/Getty Images)

Rustico Torrecampo can forever brag to his grandchildren and anyone else who will listen about how he was the first person to defeat the great, Manny Pacquiao.

In reality, it was Pacquiao’s body that robbed him of a fair chance to compete in this fight.

Pacquiao could not make the required 106 pound limit and was forced to use heavier gloves. The then 17 year old fighter had little to offer.

Torrecampo would stop Pacquiao in three rounds. After this fight, Pacquiao would jump from the Light Flyweight to the Flyweight division.

5. Miguel Cotto

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LAS VEGAS - NOVEMBER 14:  (R-L) Manny Pacquiao throws a right to the head of Miguel Cotto during their WBO welterweight title fight at the MGM Grand Garden Arena on November 14, 2009 in Las Vegas, Nevada.  (Photo by Al Bello/Getty Images)
LAS VEGAS - NOVEMBER 14: (R-L) Manny Pacquiao throws a right to the head of Miguel Cotto during their WBO welterweight title fight at the MGM Grand Garden Arena on November 14, 2009 in Las Vegas, Nevada. (Photo by Al Bello/Getty Images)

It was a war, a 2009 Fight of the Year candidate. The fight was called “Firepower” and both fighters brought plenty of it. The bout was scheduled to take place at welterweight but Cotto agreed to fight two pounds lighter at a catch weight of 145 pounds.

The two men went through a sort of feeling out process for the first six minutes but then things heated up in round three. Cotto was dropped by a glancing blow that caused him to stumble and fall. He quickly rose to his feet and from that moment, the fight was on.

Round four proved to be the best round of the fight. Cotto backed Pacquiao into the ropes and battered him with body shots. Pacquiao would respond by dropping Cotto for the second time in the fight.

Over the next seven rounds, Pacquiao out punched Cotto and eventually stopped him less than a minute into the 12th and final round.

With the win, Pacquiao became the first fighter to ever claim titles in seven different weight classes. The win solidified Pacquiao as one of the sport’s All-Time greats. His promoter Bob Arum took it a step further, “"Pacquiao is the greatest boxer I've ever seen, and I've seen them all, including Ali, Hagler and Sugar Ray Leonard,” he said.

4. Juan Manuel Marquez I

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LAS VEGAS - JULY 30:  WBA/WBO lightweight champion Juan Manuel Marquez poses on the scale during the official weigh-in for his fight against Juan Diaz at the Mandalay Bay Events Center July 30, 2010 in Las Vegas, Nevada. Marquez will defend his titles aga
LAS VEGAS - JULY 30: WBA/WBO lightweight champion Juan Manuel Marquez poses on the scale during the official weigh-in for his fight against Juan Diaz at the Mandalay Bay Events Center July 30, 2010 in Las Vegas, Nevada. Marquez will defend his titles aga

In May 2004, Manny Pacquiao was riding high. He defeated Marco Antonio Barrera in November of the previous year and was looking to prove his Featherweight supremacy by defeating IBF and WBA title holder, Juan Manuel Marquez.

Pacquiao looked great early on, dropping Marquez three times in the 1st round. Marquez wasn’t fazed by the early storm. He came back and won most of the final eleven rounds. Marquez’s classic boxing style and great counter punching kept Pacquiao at bay and frustrated him.

When it was over, the fight was very close and could have gone either way. The judges scored it 115-110 Marquez, 115-110 Pacquiao and 113-113. It was declared a draw and both fighters were reasonably angered by the outcome. It would be another three years before they would go to war again.  

3. Erik Morales I

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LAS VEGAS - MARCH 19:  Manny Pacquiao (L) of the Philippines is hit by a right hook as he throws a jab at Erik Morales of Mexico during Morales' 15-13 unanimous decision winning game over Manny Pacquiao during the World Super Featherweight Championship at
LAS VEGAS - MARCH 19: Manny Pacquiao (L) of the Philippines is hit by a right hook as he throws a jab at Erik Morales of Mexico during Morales' 15-13 unanimous decision winning game over Manny Pacquiao during the World Super Featherweight Championship at

In his 56 career fights to date, Pacquiao has only been out boxed by two fighters. One was his arch rival and greatest challenger, Juan Manuel Marquez and the other was Erik Morales.

“El Terrible,” might be the best Mexican fighter of his generation and Manny Pacquiao was up to the challenge of dethroning him. Pacquiao jumped up to 130 pounds to fight the Mexican warrior. An incidental meeting of the minds in the fifth round left Pacquiao with a nasty cut near his right eye.

The two waged an epic war and traded big shots and rounds all the way to the final bell. In the end, Morales prevailed by unanimous decision winning 115-113 on all scorecards.

On a side note, the two would meet less than a year later and Pacquiao would exact revenge courtesy of a tenth round knockout. It was the first time Morales had ever been stopped in his career. They would fight a rubber match ten months later and Pacquiao would come away the victor in that contest as well, via a third round knockout.

2. Juan Manuel Marquez II

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LAS VEGAS - MAY 7:  Juan Manuel Marquez celebrates defeating Victor Polo during their bout on May 7, 2005 at The Mandalay Bay in Las Vegas, Nevada. Juan Manuel Marquez won by points after  twelve rounds.  (Photo by Nick Laham/Getty Images)
LAS VEGAS - MAY 7: Juan Manuel Marquez celebrates defeating Victor Polo during their bout on May 7, 2005 at The Mandalay Bay in Las Vegas, Nevada. Juan Manuel Marquez won by points after twelve rounds. (Photo by Nick Laham/Getty Images)

The only thing more dangerous than taking a fight with Juan Manuel Marquez, is taking a second fight with him. Manny Pacquiao was willing to push his luck and signed up to fight Marquez a second time in March of 2008. The fight was titled “Unfinished Business,” and took place at Junior Lightweight.

The fight lived up to the hype and had it not been for the third epic battle between Israel Vazquez and Rafael Marquez (Juan Manuel’s brother) it would have won fight of the year.

Once again, it was twelve rounds of Pacquiao coming forward bringing the fight to Marquez and Marquez countering beautifully to back the Filipino Phenom up. They stood toe to toe for thirty six minutes in a fight that saw both men staggered by big punches.

 When it was over, the margin of victory ended up being one point in favor of Pacquiao. The judges scored it 115-112 for Pacquiao, 115-112 for Marquez and 114-113 for Pacquiao. The difference on the final judge’s scorecard was a third round knockdown Pacquiao scored on Marquez.

Marquez and his camp wanted to setup a third fight between the two. Pacquiao wisely declined stating, “I don’t think so. This business is over.”  

1. Getting Floyd Mayweather In The Ring

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LAS VEGAS - MAY 01: Floyd Mayweather Jr. in action against Shane Mosley during their welterweight fight at the MGM Grand Garden Arena on May 1, 2010 in Las Vegas, Nevada. Mayweather Jr. defeated Mosley by unanimous decison.  (Photo by Jed Jacobsohn/Getty
LAS VEGAS - MAY 01: Floyd Mayweather Jr. in action against Shane Mosley during their welterweight fight at the MGM Grand Garden Arena on May 1, 2010 in Las Vegas, Nevada. Mayweather Jr. defeated Mosley by unanimous decison. (Photo by Jed Jacobsohn/Getty

What could be tougher than a fight with Juan Manuel Marquez? No, it’s not Saturday’s fight with Antonio Margarito nor any other contest Pacquiao has had in his brilliant career. Pacquiao’s toughest fight is getting the uber talented Floyd Mayweather Jr. in the ring with him

Fight negotiations have stalled twice between the two fighters’ stables and the finger pointing and name calling is better suited for a grammar school playground.

Nonetheless, Floyd Mayweather and Manny Pacquiao are the two best boxers on the planet and the two best boxers of the past twenty years not named Roy Jones.

Should Pacquiao win on Saturday as he is favored to do. He, Bob Arum and Freddie Roach need publicly call out Floyd Mayweather and demand the fight be made. The fans want and deserve it and it can only serve to enhance both men’s legacies.

If the fight with Mayweather were to ever take place, Pacquiao’s greatest triumph would take place long before the first bell rang. Just getting Mayweather in the ring would be a victory in itself.   

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