When we hear the name Floyd Mayweather Jr., one thing comes to mind—his flawless, undefeated record. The man went 50-0 in the ring. Bagged 15 major world titles across five weight divisions, from super featherweight to light middleweight. That’s no walk in the park. Even after hanging up his gloves in 2017, the boxing world still holds him in the highest regard. Now, with Canelo Álvarez set to face Terence Crawford in September, fans are buzzing. Many are wondering if Bud Crawford can follow Money Mayweather’s playbook—the same one that saw the then 36-year-old outclass a young Canelo back in 2013.
But here’s the thing—while Mayweather’s record is spotless on paper, not everyone buys into its perfection. Over the years, there have been a few fights where fans and analysts alike have raised an eyebrow, questioning whether Floyd Mayweather truly deserves his 50 wins. Some of these controversial bouts have faded from memory, but today, we’re digging them back up. Let’s talk about three fights where the boxing world felt the Pretty Boy might’ve slipped away with a win—from right under his opponent’s nose.
1. Floyd Mayweather Jr. vs. José Luis Castillo I
Alright, let’s talk about one of the most debated fights in Floyd Mayweather Jr.’s career—his first bout against José Luis Castillo on April 20, 2002. To this day, plenty of boxing fans believe Castillo got robbed. And honestly? Looking at the numbers, they might have a point. Mayweather, already a WBC champ at 130 pounds, was moving up to lightweight. Early on, he did what he does best—sticking and moving, outboxing Castillo from the outside. Judges gave Floyd the first four rounds across the board, so everything seemed to be going his way.
But then, things started to shift. By the sixth and seventh rounds, Castillo was closing the gap, landing solid body shots and roughing Floyd up on the inside. From that point on, the fight looked like a dogfight. Mayweather even complained about a left shoulder injury, saying it happened right before fight night. Now, here’s where it gets messy. The referee, Vic Drakulich, docked Castillo a point in the eighth round for hitting on the break and later hit Mayweather with a deduction for using his elbows. However, the anger bubbled when the fight ended. The crowd? They weren’t buying it—boos rained down when Floyd Mayweather was declared the winner.
Even HBO’s unofficial scorer, Harold Lederman, had it 115-111 for Castillo. But here’s where opinions split—Associated Press scored it 115-111 for Floyd, while Dan Rafael of USA Today had it even at 114-114. So yeah, it was controversial. To his credit, Mayweather ran it back immediately in a rematch (one of his very few) and won decisively, shutting down the debate about his shoulder. But still, for some boxing fans, this fight will always be the one where Floyd might have gotten away with one.
2. Marcos Maidana Pushed Floyd Mayweather Jr. to His Limit
Marcos Maidana vs. Money Mayweather fight on May 3, 2014, at the MGM Grand was one of the few fights where Floyd Mayweather actually looked human. The reason you ask? Well, most of the time, when the Grand Rapids native steps in the ring, we would always see him either on defense or counterpunching. But that night? The El Chino came in like a wrecking ball. From the opening bell, the Argentine fighter went full throttle. To make things worse, he even smothered Pretty Boy with punches from wild angles. So much so that the latter was roughing him up against the ropes. Ultimately, for once, Money Mayweather looked uncomfortable.
But did he request to stop the fight? No. How could he? Floyd Mayweather did what he does best. Adjustment. His ring IQ kicked in, and by the later rounds, he started finding his rhythm, landing crisp counter shots. When the dust settled, the judges had the fight scored 114-114, 117-111, and 116-112 all in favor of Money Mayweather. That fight gave him a majority decision win. Imagine giving a tough fight and still losing in the end! Maidana wasn’t having it, though. After the fight, fumed over the decision, the 35-5 boxer stated: “I definitely think I won. Floyd had never been hit by a man before… and I still gave him a great fight. He did dominate some rounds but the majority, I dominated them.”
With all the controversy, a rematch was inevitable. Four months later, on September 13, 2014, they ran it back—but this time, Floyd Mayweather was fully prepared. He made the necessary adjustments and dominated Maidana in a cleaner, more tactical fight, winning by a unanimous decision (115-112, 116-111, 116-111). Love him or hate him, you have to admit—when it comes to adapting and winning, Money Mayweather always finds a way.
3. Playing Safe With Floyd Mayweather Jr. Backfired Oscar De La Hoya
Let’s rewind to May 5, 2007—the night Oscar De La Hoya and Floyd Mayweather Jr. squared off in one of the biggest fights in boxing history. Two absolute legends from different eras, both Olympic medalists, and both dominant champions. But as we all know, when two warriors step into the ring, only one can have their hand raised.
Boxing: Oscar De La Hoya vs Floyd Mayweather Jr. Weigh-In May 4, 2007 Las Vegas, NV, USA Oscar De La Hoya and Floyd Mayweather Jr. face off at the weigh-in for their upcoming fight at the MGM Grand Garden Arena. Las Vegas Nevada UNITED STATES, EDITORIAL USE ONLY PUBLICATIONxINxGERxSUIxAUTxONLY Copyright: xEdxMulholland-USAxTODAYxSportsx 2194494
That night, it was ‘Pretty Boy’ who walked away with the split decision victory—but if you ask De La Hoya, he still believes he should have won. “When you are a fighter inside the ring and you hear the final bell rings, you know it in your heart, in your gut, and physically if you won or you lost. You just feel it, it’s a sensation,” he explained in an interview with Club Shay Shay last year. And in that moment? He felt like he had done enough to beat Mayweather. After all, it was only the previous year when he defeated Ricardo Mayorga in a 6th-round TKO victory. But here’s the thing—feelings don’t win fights. Scorecards do.
At the time, Money Mayweather was just entering his prime, while De La Hoya was nearing the end of his career. Despite that, Oscar put up a solid fight. But in hindsight, he realized his strategy backfired. “You start thinking okay if I just cruise here, land a few punches, I have the first half won already, so if I could just one more round I can win the fight, 7-5, maybe a draw,” the Golden Boy admitted.
But playing it safe? That was his downfall. He admitted, “Obviously that night it was a big mistake.” While Oscar De La Hoya went on to fight twice more before retiring, Floyd Mayweather only got better—eventually retiring undefeated at 50-0 and becoming one of the richest athletes in the world. Looking back, De La Hoya still takes pride in going toe-to-toe with prime Mayweather, even if he fell just short.
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