Floyd Mayweather, often dubbed “Money” for his lucrative career, is one of the most celebrated boxers in history. His unbeaten record and flashy persona have earned him a place among the sport’s elite. However, behind his aura of invincibility, there have been opponents who have truly tested his mettle and made him fear for his life in the ring. Let’s delve into some of these legendary boxers who have given Mayweather sleepless nights.

1. José Luis Castillo

José Luis Castillo is perhaps the most significant name that comes to mind when discussing fighters who pushed Mayweather to his limits. In their first bout in April 2002, Castillo, with his relentless pressure and body shots, gave Mayweather one of the toughest fights of his career. Many spectators and analysts believed Castillo won the fight, but Mayweather walked away with a controversial unanimous decision. This bout was so contentious that it necessitated an immediate rematch, where Mayweather secured a more decisive victory. Nonetheless, Castillo remains one of the few to have rattled the undefeated champion.

2. Marcos Maidana

Marcos Maidana, the hard-hitting Argentinian, faced Mayweather twice in 2014. Known for his aggressive and unorthodox style, Maidana managed to rough up Mayweather in their first encounter. The bout was intensely physical, with Maidana using his wild swings and relentless pressure to put Mayweather on the back foot. Despite Mayweather winning both fights, Maidana’s tenacity and power shots left a lasting impression, proving that even the best can be put under immense pressure.

3. Shane Mosley

Shane Mosley, a seasoned veteran and former champion, faced Mayweather in 2010. In the second round, Mosley landed a powerful right hand that visibly stunned Mayweather, buckling his knees and putting him in serious trouble. For a moment, it seemed like Mosley might pull off the upset. However, Mayweather’s remarkable defensive skills and composure helped him recover and dominate the rest of the fight. Still, Mosley’s brief but intense success against Mayweather remains a highlight in discussions about Floyd’s most challenging moments in the ring.

4. Miguel Cotto

In 2012, Miguel Cotto gave Mayweather one of his toughest fights in years. Cotto’s resilience, power, and technical prowess made it a highly competitive bout. Mayweather himself acknowledged that Cotto was a formidable opponent who brought out the best in him. Cotto’s ability to cut off the ring and land significant punches forced Mayweather to dig deep and showcase his exceptional boxing skills. While Mayweather won by unanimous decision, the fight was a testament to Cotto’s skill and heart.

Floyd Mayweather’s career has been characterized by dominance and skill, but these legendary boxers managed to challenge his supremacy in ways few others could. José Luis Castillo, Marcos Maidana, Shane Mosley, and Miguel Cotto are etched in boxing history not only for their own achievements but also for the moments they made the seemingly invincible Mayweather appear vulnerable. These bouts are a reminder that even the greatest can face fear and adversity in the ring, adding to the rich tapestry of boxing lore.