Former undisputed super middleweight champion Canelo Alvarez is undeniably one of the best pound-for-pound fighters of this era. Over the years, he has faced some of the toughest competition in the sport, all while building an extraordinary record. The Mexican superstar—a four-division world champion—is the very definition of boxing brilliance.

But greatness isn’t built overnight. The 34-year-old carved out his legacy fight by fight, delivering iconic moments that transformed him into the force he is today. Now, with two massive fights on the horizon, let’s take a look back at the defining moments that cemented Canelo’s place in boxing history as one of the greatest to ever step into the ring.

Beating Gennady Golovkin in their rematch (2018) – Settling the score

The trilogy between Canelo Alvarez and Gennady Golovkin remains one of the greatest rivalries in boxing history. Their first encounter in 2017 ended in a highly controversial draw, with many believing ‘GGG’ had done enough to earn the victory. Despite the debate, an immediate rematch was scheduled—though it wouldn’t take place until September 2018, after Canelo tested positive for clenbuterol and received a six-month suspension.

When they finally met again, Canelo edged out Gennady Golovkin in a thrilling rematch, winning by majority decision and silencing critics who questioned whether he could stand toe-to-toe with one of the most feared middleweights of all time. The saga came to a close in 2022 with their third and final bout. This time, Canelo left no doubt, dominating Golovkin as the Kazakh struggled to find his rhythm at super middleweight.

Stopping Sergey Kovalev – Winning a Title at Light Heavyweight (2019)

Terence Crawford might be chasing Canelo across weight classes today. But it’s worth remembering that Canelo has walked that path before. His showdown with former WBO light heavyweight champion Sergey Kovalev—a feared knockout artist in his own right—was a defining moment in his career. Stepping up two weight classes to 175 pounds, Canelo sought to claim a world title in a fourth division.

Despite giving up height and reach, he delivered in spectacular fashion. In the 11th round, Canelo unleashed a devastating knockout, proving not only that his skills could carry across divisions but that his power was just as dangerous against bigger men. The victory crowned him the WBO light heavyweight champion and cemented his place among boxing’s all-time greats.

Becoming the undisputed Super Middleweight Champion (2021) – A historic feat

Canelo Alvarez has had the most successful run in the super middleweight division and brought the weight class to public attention alone. He started by defeating Callum Smith in 2020 to acquire the WBA (Super) and WBC titles. He then moved on to fight Billy Joe Saunders in 2021 to collect the WBO title, which saw Canelo dominate the Brit like never before. 

This followed Canelo’s fight against Caleb Plant for the IBF strap, in which Canelo outboxed ‘Sweethands’ to become the first undisputed super middleweight champion. He also became the first Mexican boxer to hold an undisputed status across every weight class. This was a truly historic moment not just for Canelo but also for the division and Mexico. 

Dominating Miguel Cotto to win the Middleweight Championship (2015)

Canelo Alvarez’s win over the legendary Miguel Cotto was a turning point in the Mexican’s career, which saw him become a bona fide superstar from a promising prospect. Cotto, at the time, was seen as the sport’s elder statesman. Canelo’s win over Cotto in 2015 symbolized the passing of the torch, which established him as the new face of boxing.

Before the fight, Canelo fought in the light middleweight division. But after his victory, his ability to compete and dominate at a higher weight class against an elite opponent was validated. Not to mention, the fight was a huge success, generating 900,000 pay-per-view buys on HBO and a live gate of $12,470,200 with 11,970 attendees. This made Canelo a massive draw, especially among Mexican and Latino fans. 

Knocking out Amir Khan with a Brutal Overhand Right (2016)

Just after defeating Cotto, Canelo defended his WBC, Ring magazine, and lineal middleweight titles against speedy Amir Khan. In the 6th round of the fight, Canelo knocked out Khan with a bone-shattering overhand right on Khan’s chin. Khan’s knees buckled, and he fell backward—his head hit the canvas and bounced back. Referee Kenny Bayless didn’t take long to stop the fight after that. 

This was Alvarez’s most brutal knockout of his career, building his reputation as a devastating finisher. To add to Canelo’s legacy, the knockout was named the ‘Knockout of the Year’ by Ring Magazine. However, the most important part about the knockout was that it showcased Canelo’s power and counterpunching ability. 

Schooling Julio César Chávez Jr. in a Mexican Superfight (2017)

The clash between Canelo Alvarez and Julio Cesar Chavez Jr. didn’t come with titles on the line—but it carried something even bigger—national pride and the battle to become the face of Mexican boxing. Fittingly held during the Cinco de Mayo weekend celebrations, the all-Mexican showdown saw Canelo put on a masterclass, completely dismantling the son of the legendary Julio Cesar Chavez Sr. By the final bell, there was no doubt—Canelo had officially taken the mantle as Mexico’s boxing icon.

Shocking Callum Smith – Winning the WBA & WBC Super Middleweight Titles

The Callum Smith fight often gets lost in the pages of boxing history, but it was the moment Canelo Alvarez first asserted his dominance over the super middleweight division. Despite being the smaller fighter in the matchup, Canelo outboxed and outmatched Smith to showcase his superiority over the 168-pound division. This later took him on a path to unify all the belts and become the first undiluted super middleweight champion. 

First fight against Gennady Golovkin – A controversial classic (2017)

Even though Canelo’s first fight against Golovkin was shrouded in controversy, it was an important moment in his career. The fight had come to a split-decision draw, but many fans and experts believed Golovkin had done enough to secure a win. This motivated Canelo to come back for a rematch, which he did, establishing himself as the best fighter in the middleweight division. 

Stopping Billy Joe Saunders – Breaking his Orbital bone (2021)

The day Canelo Alvarez defeated Billy Joe Saunders was significant for the Mexican superstar. It didn’t just give Canelo the WBO belt in the super middleweight division, but it also showcased Saunders’s southpaw slickness and defensive craft wasn’t a threat to Canelo. His dominance over Saunders silenced doubters about his versatility. 

However, the same fight was disastrous for Saunders. It not only ended his unbeaten run but also ended his career. Having suffered a brutal orbital fracture during the fight, the Brit never stepped back into the ring ever again. This was especially vindictive for the Mexican, as Saunders trash-talked Canelo throughout the buildup of the fight. 

Winning his first World Title against Matthew Hatton (2011)

Before Canelo Alvarez became a worldwide sensation, his first career milestone came at the age of 20 when he won his first world title against Matthew Hatton in 2011. It marked a significant career break for the Mexican superstar, as he defeated Hatton via unanimous decision to acquire the vacant WBC light middleweight title. 

Despite his age, Canelo showed maturity beyond his years. He paced himself while overwhelming Hatton without chasing a knockout finish. Hatton might not have been the best boxer out there, but he had a decent record, which gave Canelo’s win the validation he needed to justify Golden Boy Promotions’ investment in him on the road to becoming a big star. 

And with that, we’ve walked through the decorated career of Canelo Alvarez— a journey of grit, skill, and determination that saw him climb the boxing ladder to become one of the biggest names in the sport today. Now, he finds himself on a collision course with another pound-for-pound great, Terence Crawford, this September. A victory would elevate Canelo’s legacy to unprecedented heights. But even in defeat, his incredible body of work will forever justify his place among boxing’s all-time legends. What did you think about Canelo’s legendary career?