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Cotto vs Canelo: Miguel Cotto's Five Biggest Wins

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Miguel Cotto has been on this sort of stage before, but he's never scored a win in a fight quite as big as the one he'll have Saturday against Canelo Alvarez.

JC Olivera/Getty Images

Despite the claims of Miguel Cotto and trainer Freddie Roach that Satuday night's HBO pay-per-view clash with Canelo Alvarez is "nothing special," it is. When you look over the careers of both men, this is a higher-end fight for both.

Even for Cotto, who has faced many of the top names of his era, this is a hugely important fight on paper, not just for money and accolades, but somewhat for his legacy. Cotto's two biggest fights were losses to Floyd Mayweather and Manny Pacquiao, and as good and sometimes great a fighter as he's been, there is an argument to be made that he doesn't really have a career-defining sort of victory.

Canelo, the young Mexican superstar poised to inherit the dollar-for-dollar throne in the absence of Floyd and Manny, could be the sort of win for Miguel. If Cotto, at 35, upsets the apple cart and pulls off the W against Alvarez, it could be the biggest victory of his career, which is already bound for the Hall of Fame.

What's the competition? Let's take a look at my picks for Miguel Cotto's five biggest wins.

5. Joshua Clottey (2009-06-13)

WBO Welterweight Fight: Miguel Cotto v Joshua Clottey Photo by Al Bello/Getty Images

Cotto had just regained a welterweight title, beating Michael Jennings for the vacant WBO belt in February '09, and the rugged Clottey was his first challenger. Cotto dropped Clottey on a jab in round one, but it was much tougher sailing from there, as the Ghanaian battled his way back into the fight and reminded everybody that this was a fight between top welterweights, not a Cotto mismatch.

In the end, Clottey had an argument for the victory, and there was some controversy about the scoring. But Cotto getting the split decision had a lot less to do with him fighting on home turf at Madison Square Garden than it did Clottey not throwing punches far too often, all but handing Cotto a few rounds that proved the difference in the fight.

4. Paulie Malignaggi (2006-06-10)

Paul Malignaggi v Miguel Cotto Photo by Nick Laham/Getty Images

Cotto's first pay-per-view fight shouldn't have been a pay-per-view fight, but Top Rank wanted it to be one, so they made it one. More memorable than what channel it was on was the severe beating that Cotto gave Malignaggi, whose face was a swollen, broken disaster after the 12 rounds of action.

Malignaggi proved that he was more than a trash talking pretty boy in the fight, that he was tougher than nails and could take a beating, as well as hang in the fight. For as much as it looked like Cotto truly dominated the fight, he didn't, really, winning on scores of 115-112 and two of 116-111. He was the clear victor, but Malignaggi was competitive, and Cotto didn't lose any composure when he couldn't put Malignaggi away, either, fighting his fight and getting the job done.

3. Antonio Margarito (2011-12-03)

Miguel Cotto v Antonio Margarito Photo by Al Bello/Getty Images

More a great emotional victory for Cotto than anything, his revenge rematch with Margarito in 2011 gave the Puerto Rican star some peace of mind after their 2008 fight, which Margarito had won by wearing Cotto out and stopping him in the 11th round, after Cotto had dominated the early portion of the fight. Controversy about that win for Margarito -- and about most of Margarito's career -- arose when in 2009, his team were caught with illegal handwraps containing traces of a foreign substance prior to Margarito then going out and getting brutalized by Shane Mosley.

As far as the boxing part of this goes, on that night in 2011, Margarito was a shell of what he'd been when he faced Cotto the first time. Even if we take out the idea that Margarito had operated with loaded gloves against Cotto in '08 (not that you should if you don't want to, there's reason to think he did), Margarito was no longer that same fighter. He'd been suspended for a year after the Mosley fight, and then went to Texas in November 2010 to get the crap kicked out of him by Manny Pacquiao, suffering significant facial damage.

By the time he showed up to face Cotto again 13 months later, he had a visibly damaged eye, even after surgery and time off, and probably shouldn't have been licensed to fight in the first place, something that became a story in the build-up to the bout. Cotto showed no mercy, targeting Margarito's eye and beating on it until referee Steve Smoger stopped the fight after nine, one-sided rounds.

2. Sergio Martinez (2014-06-07)

Miguel Cotto v Sergio Martinez

Again, a win that is bigger in name value perhaps than actual value. The Margarito win could be here because it was probably more personally important to Cotto. While Margarito hadn't fought in a year and was beaten viciously that previous time out, Martinez was also clearly not quite himself anymore, either. With repeated knee injuries, age, and conditioning all a factor, Sergio looked like he'd slid in his own previous fight, a debatable 12-round decision over Martin Murray. And like Margarito, Martinez had not fought in over a year when he did get in with Cotto.

Still, Sergio was one of the world's best fighters from 2010-13, when he reigned as middleweight champion of the world and beat everyone put in front of him. Cotto, coming up from junior middleweight, was small as a middleweight (and still is), but he ferociously went after Martinez to start the fight, dropping "Maravilla" three times in round one. The fight didn't really become any more competitive. When it was stopped six seconds into the tenth round, with Martinez unable to continue, Cotto was leading 90-77 on all scorecards. It was a one-sided wipeout. What percentage of that is due to Martinez being physically shot is up for you to decide or debate, but it was still a big win for Cotto, and really set up this fight with Canelo Alvarez, too.

1. Shane Mosley (2007-11-10)

Miguel Cotto v Shane Mosley Photo by Al Bello/Getty Images

While it would be hard to say that Mosley was in his prime in 2007 -- he was 36, after all -- he was still a legitimate top tier welterweight, and the first that Cotto had faced, unless you want to count Zab Judah, which I do not because Judah hadn't won a fight in two years when Cotto beat him, and had lost to Carlos Baldomir.

Mosley was there step-for-step with Cotto, battling the younger man every step of the way in a competitive, high-level welterweight title fight that lived up to expectations. The veteran Mosley looked quick and strong, and won his share of the fight, but the decision to Cotto was clean and clear. There was no argument when he had his hand raised on scores of 115-113, 115-113, and 116-113, but he'd been gut checked, and came out a better fighter for it.