5 of the Best Middleweight Boxing Matches Ever

A significant percentage of the best boxers ever to step into the ring have competed as middleweights. From Sugar Ray Robinson to Marvin Hagler, middleweight boxers have been responsible for some of the greatest fights in the history of the sport. Looking back chronologically on the division, let’s examine five of the best middleweight bouts of all time.

1. Harry Greb vs. Mickey Walker (July 2, 1925)

Two titleholders came together for this 1925 clash, which was held before 50,000 fans at the Polo Grounds. Welterweight champion Mickey Walker — nicknamed “The Toy Bulldog” for his propensity as a smaller man to beat bigger fighters — came up in weight to challenge Harry Greb, then the middleweight champion.

Just five months earlier, Walker had beaten a light heavyweight, and he nearly repeated the feat of felling a bigger man in Greb. The contest was close throughout, with the pace quickening in the later rounds. It was in the 14th round, however, that Greb took control to secure a unanimous decision.

While Walker came up short in the ring, legend has it that he exacted a measure of revenge out in the New York City streets. The story goes that the two boxers ended up at the same nightclub the evening after the bout and, after commiserating over a few drinks, left together.

When Greb started taking off his coat in preparation to continue their fight, Walker socked the bigger man in the face. Many have cast doubt on the veracity of this version of events, but at the very least, the (probably) tall tale adds a bit of lore to what is one of the middleweight division’s classic bouts.

2. Rocky Graziano vs. Tony Zale (July 16, 1947)

Tony Zale scored an emphatic sixth-round knockout of Rocky Graziano in the first brawl between these two middleweight greats. Just 10 months later, in front of a record crowd at Chicago Stadium, “Rocky Bob” looked to even the score.

His chances at doing so looked bleak early on, as “The Man of Steel” subjected his opponent to a one-sided beating that left Graziano with a mangled face. Despite his injuries, Graziano stormed back. After a punch nearly sent his opponent through the ropes, the referee called the fight for Rocky Bob.

The pair met in the ring once more in a trilogy that boxing journalist Red Smith called “the most two-sided fights ever.” Of their three memorably brutal bouts, it’s this one, their second, that boxing afficionados place the among the greatest fights of all time.

3. Carmen Basilio vs Sugar Ray Robinson (September 23, 1957)

Sugar Ray Robinson spent his best years at welterweight, but he did rise to the top of the middleweight division and, at the age of 37, was still in fine form at the time of this 1957 contest. Challenging him for the middleweight crown was welterweight champion Carmen Basilio.

Widely considered the greatest boxer of all time, the skillful, athletic Robinson faced an especially stiff test against the brawling Basilio, who along with being seven years younger was known for his ability to withstand an unusual amount of punishment. The clash in styles made for a particularly exciting matchup.

The fight lived up to the hype, and the 40,000 fans at Yankee Stadium witnessed a thrilling contest with numerous swings in momentum. The back-and-forth fight ultimately went to the scorecards, where Basilio prevailed via split decision.

4. Marvin Hagler vs. Thomas Hearns (April 15, 1985)

The legendary bout brought together two fighters who, at the time, were perhaps the greatest boxers in the world. Marvin Hagler was the undisputed middleweight champion of the world, while Thomas “Hit Man” Hearns was coming up in weight after winning a 154-pound belt. So great was the anticipation for this matchup that it was billed simply as The Fight.

The fireworks started immediately, with both fighters rocking each other in a spectacularly violent first round that’s considered among the best three minutes in boxing history. More brawl than boxing match, Hagler-Hearns saw the competitors trading blows like they were duking it out on the Las Vegas streets instead of going head-to-head in a sold-out Caesars Palace.

Hagler got a cut in the first round that bled profusely, but he marshalled his strength to knock out Hearns in the third round. Although it only lasted eight minutes, the bout was so hellacious that boxing fans realized The Fight moniker no longer fit. Henceforth, Hagler-Hearns would be known as The War.

5. Marvin Hagler vs. Sugar Ray Leonard (April 6, 1987)

Two years after The War, Marvin Hagler remained at the top of the middleweight division, where he was in the midst of an 11-year unbeaten streak. His most recent fight had been a brutal contest against John Mugabi. While Hagler finished “The Beast” in 11 rounds, some ringside observers noticed the 32-year-old champion had begun to show some signs of aging.

Among those observers was Sugar Ray Leonard. An all-time great whose résumé included wins over the likes of Hearns and Roberto Duran, Leonard decided the time was right to come out of retirement to face Hagler.

Leonard, who had stepped into the ring only once in the previous five years — and never before at middleweight — used his speed and savvy to keep the contest close. After 12 competitive rounds, the fight went to the scorecards. Despite coming into The Showdown as a significant underdog, Leonard prevailed, edging out a controversial split decision that boxing fans still debate today.



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Harvey Bell

Harvey Bell serves as a managing director, team leader, and senior portfolio manager with Morgan Stanley in West Orange, New Jersey.