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Floyd Mayweather Jr. stepped into the ring with some of the best boxers in the sport during his career.
Between 2005 and 2015, Mayweather's fights included bouts with Manny Pacquiao, Arturo Gatti, Ricky Hatton, Oscar De La Hoya, Canelo Alvarez, Zab Judah, Marcos Maidana, Juan Manual Marquez, Miguel Cotto, Shane Mosley, and Carlos Manuel Baldomir.
By 2005, Mayweather already had more than thirty fights under his belt. He shared the ring with the likes of Diego Corrales, Jose Luis Castillo, and Emanuel Augustus. When he retired in 2015, he had a record of 49-0-0 with 26 knockouts.
Though Mayweather never lost a fight, not all of his wins came easy. Here's a look at five of the hardest fights in the contemporary great's career.
5. Floyd Mayweather Jr. vs. Shane Mosley
One of Mayweather's toughest fights came in 2010 when he fought 'Sugar' Shane Mosley at the MGM Grand in Las Vegas, Nevada. Mosley entered the ring with a record of 46-5-0. He was coming directly off his devastating knockout win over Antonio Margarito. Mayweather was coming off back-to-back wins over De La Hoya, Hatton, and Marquez.
Mosley, who earned 41 of his 49 career wins by knockout, had the power to end the fight early. In fact, he caught Mayweather with a right hand early in the second round that nearly dropped 'Pretty Boy'. About a minute later, he was caught flush with a second right hand that caused his knee to buckle.
Mosley forced Mayweather to the ropes and attempted to finish the job. However, Mayweather managed to hold on for the remainder of the round. Though the bout was not the toughest in terms of bell-to-bell fighting, it was probably the closest the unbeaten fighter ever was to being knocked out.
Check out Mayweather vs. Mosley here:
4. Floyd Mayweather Jr. vs. Jose Luis Castillo
On April 20, 2002, Floyd Mayweather Jr. stepped into the ring with Jose Luis Castillo. The WBC and The Ring Lightweight Titles were on the line. Castillo had claimed the WBC Title from Stevie Johnston two years prior. It was his fourth title defense.
Castillo vs. Mayweather I is one of the most contested victories of Mayweather's career. Early in the fight, Mayweather established dominance with a powerful lead hook and a sharp jab. In the first round, Castillo landed just three punches. Yet, as the rounds progressed, he took control of the center of the ring and began to force the challenger onto his backfoot.
The Mexican champion came forward with effective aggression in the later rounds and the two men were forced to fight back and forth. When the final bell rang, Mayweather was awarded the victory. As the decision was contested by many, Mayweather and Castillo fought a rematch later that year. Mayweather won via unanimous decision.
3. Floyd Mayweather Jr. vs. Marcos Maidana
In 2014, Floyd Mayweather Jr. had two back-to-back fights with Marcos Maidana. Maidana stepped into the ring for the first bout with a record of 35-3-0. He lost both fights to Mayweather and then retired from boxing.
The first fight between Mayweather and Maidana was one of the toughest bouts of the former's career. The Argentinian great took the fight to Mayweather and relied on strength and aggression to pin the champ to the ropes. He landed devastating overhand rights and kept the American off balance with hard rushes.
Throughout the early rounds, Mayweather landed enough effective counterpunches to stay in the judges' favor. As the fight progressed, he managed to gain control of the ring again. It was one of the closest toe-to-toe battles of his recent career but the champion edged the decision on the scorecards.
As with Castillo, Mayweather left nothing to chance and took an immediate rematch with Maidana. In the rematch, he fought another tough battle but claimed a more decisive victory still.
Check out Maidana vs. Mayweather here:
2. Floyd Mayweather Jr. vs. Emanuel Augustus
On October 21, 2000, Floyd Mayweather Jr. stepped into the ring with Emanuel Augustus, 'The Drunken Master'. Augustus is renowned as one of the best fighters in modern history, though he did not have the opportunity or dedication to reach the peak of the sport.
At the time of the fight, Augustus had a record of 22–17–4. It is said that his losses were largely due to bouts that he took without preparation. When he stepped into the ring with Mayweather, he was ready for a fight. His unorthodox style tested Mayweather's capabilities and forced the younger boxer to use all of his talents.
After the fight, Mayweather said that Augustus was his toughest opponent to date. As Boxing Scene reports, the fighter said:
"Emanuel Augustus was my toughest fight. He was tough. At that particular time, that was my longest layoff. I was a fighter who was active and fighting every three or four months. I took nine months off and fought a guy who was active and he made me bite down. It was a great night."
The following year, Augustus and Micky Ward had another hard contest which was awarded 2001's fight of the year.
1. Floyd Mayweather Jr. vs. Miguel Cotto
Miguel Cotto and Floyd Mayweather Jr. fought on May 5, 2012. It was another tough contest for Mayweather, who was hit clean with more shots than he was used to. Though it may not have been the closest fight of his career, it was definitely one of the hardest.
With a strong jab, Cotto kept Mayweather out of rhythm and managed to establish his own range. His shots landed flush and drew blood from 'Pretty Boy', thus named for his apparently unnatural ability to avoid damage in a fight. Boxing Scene reported that Mayweather later said:
"Emanuel Augustus was tough, Miguel Cotto was tougher. Miguel Cotto was the toughest fighter that I've faced thus far. What Miguel Cotto did was try to come on strong in the later rounds, which made me fight harder."
Check out Mayweather vs. Cotto here:
