The Ten Toughest Fights of Floyd Mayweather’s Career

By Tyson Bruce

This Saturday on Showtime PPV Floyd Mayweather Jr. will fight in just the second rematch of his Hall of Fame career. In an eighteen year career that has be defined by utter dominance we set out to uncover the ten toughest fights in Mayweather’s entire career:

Photo: Showtime

1. Jose Luis Castillo I (2002): This is pretty much the only fight on Mayweather’s record that you could make a convincing argument he deserved to lose. Castillo’s reputation has taken such a battering in recent years from blowing off making weight and declining ring performances that many people have forgotten what a formidable fighter he was in his prime. When Mayweather fought Castillo he hadn’t lost in almost four years and had recently defeated the very excellent Stevie Johnston. Mayweather, unknown at the time, went into the bout with a badly injured left shoulder.

Mayweather used his footwork and razor sharp reflexes to keep Castillo largely at bay for the first five rounds until Castillo worked his way into the fight with a withering body assault and an assortment of flagrant fouls. Castillo lost a point in the eighth round for hitting on the break (he did this repeatedly throughout the bout). The always-awful Rick Drakulich struck again in the ninth round when he evened the score by taking a point away from Mayweather for using his elbows. The judges scored the bout 115-111 (twice) and 116-111 all for Mayweather, which was booed loudly by the pro-Mexican crowd. Interestingly, Harold Letterman scored the fight 115-111 for Castillo—the only fight on record that Letterman did not score in favor of Mayweather. The bout was controversial enough that Mayweather fought an immediate rematch with Castillo.

2. Marcos Maidana (2013): There is no question that Mayweather underestimated Maidana—if not physically than mentally. How could he not? Maidana wouldn’t be favored to beat many of the top fighters Mayweather has defeated over the years and yet the Argentine gave Mayweather one of his most epic struggles. Make no mistake at the midway point of the fight Mayweather was in the hole and had to fight his way out of it the second half of the bout. Maidana’s wild and unpredictable assaults gave the ultra-technical Mayweather fits. For the first time in ages—maybe ever—Floyd didn’t seem to know how to solve the puzzle in front of him.

Fortunately for Mayweather, his stamina is second-to-none and he thinks well in late stages of fights better than just about any fighter in recent boxing history. Mayweather gradually increased his punch output and brought the fight into the center of the ring where his faster hands could have a greater effect. Even though Mayweather could never hurt Maidana, his greater technique prevailed by way of a razor thin majority decision, with scores reading: 117-111 (ridiculous), 116-111 and 114-114.

3. Oscar De La Hoya (2007): In what was the high selling PPV fight in the history of boxing (it sold 2.7 million units), Mayweather won a non-controversial but close unanimous decision over his nemesis Oscar De La Hoya. The fight was deemed by the mainstream press as “the fight to save boxing” but instead turned out to be a tactical affaire where nothing memorable happened. Still, the bout was groundbreaking and changed forever the way a PPV event would be marketed.

De La Hoya came out with an excellent game plan that consisted of using his jab and size to bully Mayweather to the ropes where he could out-hustle his faster opponent. De La Hoya built a slim lead on the scorecards by the mid-way point of the bout before his stamina and jab went to ruin. Mayweather began to get into the zone and hummed De La Hoya repeatedly with right hands over Oscar’s now lazy jab. If this fight had happened in 2003 instead of 2007 who knows how it might have gone, but on this night Mayweather was superior if not all that impressive. It still stands as the only split decision victory in Mayweather’s entire career.

4. Miguel Cotto (2012): Many experts are convinced that Mayweather ducked Cotto in the late 2000’s when the Puerto Rican was in his prime. Their 2012 fight could be proof of this, as Mayweather had a titanic struggle against a version of Cotto that many viewed as years past his best. Cotto came with a brilliant strategy of using a stiff jab right up the middle to break Mayweather’s shoulder roll defense. At times, most notably in a dominant eighth round for Cotto, it worked brilliantly. Cotto bloodied Mayweather’s nose and lumped his face up in way very few fighter ever have. Mayweather, however, was never really in danger of losing the bout. His faster hands and superior stamina were always going to win out and he dominated the championship rounds in what was one of the most entertaining fights of his career.

5. Jesus Chaves (2001): This is one of the most entertaining yet little known fights in Mayweather’s entire career. The match was absolutely brutal for as long as it lasted and showcased a very different and more offensive version of Mayweather in his prime. Chavez was riding a 31-bout win streak going into the bout and was determined to give Mayweather hell. He did just that by pinning Mayweather against the ropes with a near constant stream of aggression and body punching. Mayweather showcased his brilliant (and underrated) ability to fight in the pocket by rolling with Chavez’s punches and rocketing him back with vicious uppercuts and right hands. Mayweather had reportedly struggled mightily to make the 130-pound limit and, therefore, must be given credit for pulling out ahead in such a brutal affaire. The bout ended in the ninth round when Chavez’s trainer Ronnie Shields surprisingly stopped what had been a competitive fight up to that point.

6. Carlos Hernandez (2001): This fight wasn’t tough in a competitive sense but it stands out as one of Mayweather’s greatest physical struggles because he fought much of the bout against the world-class Hernandez with a shattered left hand. In fact, Mayweather suffered the only “official” knockdown of his entire career when, after hitting Hernandez with a left hook in the sixth round, Mayweather went to canvas withering in pain. Mayweather looked like he was in excruciating pain and must be given enormous credit for fighting through a brutal injury and not submitting. It came during a stretch between 2001-2003 when Mayweather struggled in just about every fight from hand problems. It proved that Mayweather, despite his flashy defensive style, is all-fighter when it counts.

7. Emanuel Augustus (2000): The fight took place on the now defunct HBO-fight series “KO Nation” and was Mayweather’s first fight since firing his father as trainer in favor of his uncle Roger Mayweather. In the fight we saw the transition of Mayweather’s style from a pure boxer into more of a boxer-puncher. Augustus (then Burton) is one of the most gifted fighters in the history of boxing to have a 50-50 record and pushed Mayweather with his wonky technique and otherworldly courage. Augustus took a sadistic amount of punishment from Mayweather but often replied with a smile and volley of punches in return. Augustus probably didn’t win a single round but Mayweather often states in interviews that it was one of his toughest nights in the ring. The bout was stopped in the ninth round to save Augustus from taking anymore unnecessary punishment.

8. Zab Judah (2006): Many people would probably place this fight much higher on the list than number eight but they would be forgetting just how utterly one-sided this fight was from about round five onwards. Still, Judah, with his absurd hand speed, gave Mayweather a few legitimate scares early on. Judah is one of the few fighters Mayweather has ever boxed that had faster hands than he did and it took a prime Mayweather a few rounds to figure the Brooklyn product out. Judah was probably deprived of scoring a knockdown when he clocked Mayweather with a straight left hand that caused Mayweather’s glove to touch the canvas in round two. In the fifth round Mayweather began to take over the fight and proceeded to dole out a vicious beating from that point forward. In fact, its very likely Mayweather would have scored a stoppage victory had the melee in round ten not occurred. The final scores were 116-112, 117-111 and 119-109 all for Mayweather.

9. Jose Luis Castillo II (2002): The rematch to Mayweather’s greatest struggle as pro was a much more decisive albeit still challenging victory. Mayweather used a great deal more lateral movement, combination punching and jabs to keep the rugged Mexican at bay. Castillo, ever the competitor, remained competitive in a fight that was utterly devoid of any notable exchanges. Mayweather, probably still feeling the effects of the first bout, never took any chances in the rematch and boxed very cautiously. It was yet another display of Mayweather’s unique ability to make adjustments in the ring. The scores, however, reflected the closeness of the bout: 115-113 (twice) and 116-112. Ironically, the scores for the rematch were much closer on all three cards than the first bout where it is felt Castillo fought much better.

10. DeMarcus Corley (2004): The bout was Mayweather’s first foray into the 140-pound weight class and it proved to be a thrilling one. The vastly underrated Corley managed to rock Mayweather on several occasions, most notably in the third and forth rounds. Mayweather responded beautifully to Corley’s challenge by eventually dominating the inside exchanges with a withering assault of combination punching. Mayweather dropped Corley in the eighth and tenth rounds and only Corley’s immense courage kept him standing until the final bell. Mayweather showed in the bout that he had the ability to withstand some massive punches as well as possessing sublime recuperative powers.