The Best Boxers of All Times and Their Greatest Fights

#1 Sugar Ray Robinson

Sugar Ray Robinson is often considered the greatest pound-for-pound boxer in history. His combination of speed, power, and technical skill set the standard for what a boxer could be. Robinson’s dominance in the middleweight division, as well as his success in other weight classes, makes him a standout figure in the sport.

Most people know Ali, but true boxing fans know that he revered and modeled his style after Sugar Ray Robinson. Pound for pound, Robinson is the best boxer of all times because he dominated both the welterweight and middleweight divisions with a record of 173 wins, 19 losses, and 6 draws, with 108 of those wins coming by knockout.

At one point, he went on a 91-fight unbeaten streak, which is absolutely insane to think about, regardless of the sport. It’s something that veteran boxing bettors haven’t seen since those years.

Robinson had it all: speed, power, footwork, and ring IQ. Basically, this guy could knock you out with either hand, and was quick enough to adapt to your fighting style, which made him nearly unbeatable during his prime. He set the gold standard for modern boxers, blending athleticism, skill, and strategy in a way that no one before (or since) has fully matched while advancing the sport, as a whole, into modernity.

Sugar Ray’s footwork was on another level. He floated, or danced around the ring to control the pace of the fight and stay out of danger and to set up his own attacks. His head movement, positioning and footwork were all part of his defensive game, but once Robinson went on the offense, terror came with him.

His punches were lightning-fast, and he had the unique ability to throw combinations with both hands which made it near impossible to know where the next punch would come from. The jabs were sharp and precise, but his right’s uppercuts and hooks would usually seal the deal, the problem was, as always: when would they strike? You can feel how terrifying it must be to go against a fighter that adapts to your pacing and style mid-fight and somehow manages to punch harder and faster than you. This technical superiority is what really put the fear in his opponents.

Here are some of his most iconic fights:

Sugar Ray Robinson vs. Jake LaMotta Series (1942-1951)

Robinson and Jake LaMotta fought six times, with Robinson winning five of those matches. It all started in the famous “St. Valentine’s Day Massacre” in 1951, where Robinson handed LaMotta one of the worst beatings in boxing history to win the world middleweight title. LaMotta was tough as nails, but it got so bad that the referee had to stop the fight in the 13th round, and many argue the referee should’ve ended it sooner.

Sugar Ray Robinson vs. Gene Fullmer (1957)

Gene had managed to beat Robinson earlier that year, and he was very eager to avenge this loss. In this fight, Robinson delivered one of the most famous knockouts in boxing history, landing a perfectly timed left hook that floored Fullmer. This punch is used to teach hook timing to modern boxes, even today!

Sugar Ray Robinson vs. Kid Gavilan (1949)

Robinson fought Kid Gavilan twice, and both of these fights were, by all accounts, incredible fights between two warriors. Their second fight was simply on another level, though. Gavilan was completely outclassed by Robinson, who channeled the gods of boxing through his gloves and dominated an extremely tough boxer from start to finish.

Keep in mind that Sugar Ray Robinson dominated both the welterweight and middleweight divisions, and he dodged no one. He won the welterweight title and later moved up to win the middleweight title five times and showed the same level of technical superiority and speed that modeled modern boxing to this day.
His 91-fight unbeaten streak, 200 fights, two decades at the top and the tremendous quality of his opponents only cement his well-deserved spot as the best boxer of all times.

His 91-fight unbeaten streak, 200 fights, two decades at the top and the tremendous quality of his opponents only cement his well-deserved spot as the best boxer of all times.

#2 Muhammad Ali

Someone said that Muhammad Ali was the greatest boxer of all time, not the best boxer of all times, and I couldn’t agree more. Ali’s career was marked by extraordinary achievements, including winning the heavyweight title three times (he’s in fact the best heavyweight boxer of all times), but Sugar Ray Robinson wins in the overall ranking because of two factors:

1. Ali couldn’t fight during two years of his prime as a fighter
2. Many believe he should’ve retired sooner, but who can blame him?

The fact is that Ali, at his prime, was untouchable. Admittedly, I’m biased, in fact l think that during his prime he was even better than Sugar Ray Robinson, but when comparing their careers from start to finish, he has to surrender the first spot.

His ability to “float like a butterfly, sting like a bee” revolutionized the sport, combining speed, agility, and power to outwit and outpunch his rivals during legendary fights that entered the sport’s lore. Ali was also the greatest boxer of all times because he was a cultural icon who transcended sports, because of his iron will, tremendous charisma and unnatural talent to beat the odds.

I already discussed some of his most iconic fights on another piece, but I’m a sucker for these fights, so let’s head down memory lane.

Liston vs Ali in 1964

This career put Ali (Cassius Clay back then) in the spotlight, when he went against the intimidating Sonny Liston as a 7-to-1 underdog. Liston was the heavyweight championship and, perhaps, the most intimidating figure in modern boxing, and Ali had forced this beast of a man to quit on his stool after the sixth round. It was the stuff of legends.

The Rumble in The Jungle

You can’t go over Ali’s career without mentioning this fight. Foreman was an undefeated champion that had knocked out most of his opponents, to the point where he had rarely fought past the 4th round. He was convincingly dominating his opposition with sheer power, and many thought he’d also roll over Ali.
But analysts back then were comparing physiques and forgot that Ali’s wits were just as fearsome as his jabs and speed. He used his “Rope-a-Dope” strategy and leaned against the ropes, letting Foreman punch himself out, patiently waiting for an opening. In the eighth round, Ali took his shot and knocked Foreman out with a devastating flurry of punches to prove that his tactical brilliance put him at the top of the sport.

Thrilla in Manila

Ali’s and Frazier final fight was fought in intense heat, with both warriors pushed to the absolute limit. After 14 brutal rounds in the suffocating heat, Frazier’s corner stopped the fight just before Ali’s corner could. According to his biographer, Ali at one point thought he was about to literally die, and asked (seconds before Frazier’s surrender) to cut his gloves to end the fight. The fight was the greatest and most brutal fight in boxing history, and if you’re a newer fan of the sport, you’d do well to watch it.

Muhammad Ali fought during the golden age of heavyweight boxing, and he faced some of the toughest opponents in history, never dodging a challenging fight. Liston, Frazier, Big George were tremendous rivals and he faced all of them. His reflexes, speed, ring IQ and technical brilliance made him the second-best boxer of all time, narrowly below Sugar Ray Robinson.

I can’t help but think that he would’ve surpassed him if he hadn’t lost two years of fighting at his prime, but I’m a Muhammad Ali fanboy, so take it with a grain of salt.

#3 Henry Armstrong

Armstrong boxed from 1931 to 1945 and, at one point, held three world titles in different weight classes at the same time. That’s right, he was the world champion in featherweight, lightweight, and welterweight divisions at a time when there were only eight weight divisions. It’s an insane thing to even consider, but Henry did it thanks to his relentless fighting style, stamina and talent.

Henry’s style could only be described as shock and awe: he’d swarm his opponents with a powerful barrage of punches throughout the fight to physically and mentally overwhelm them. The idea was to stablish non-stop pressure and pain before the opponent could think of a way to adapt to the onslaught. His body shots were devastating and would turn his opponents into a bruised bag of bones and meat until they were unable to defend themselves.

Naturally, this style would require tremendous stamina, strength and guts to work, but Henry had plenty of all.

Henry defended his title 19 times and in 1939 fought a total of 16 times, which is crazy to even consider, especially due to his high-intensity and physically taxing fighting style. Let’s go over some of his most iconic fights:

Armstrong vs. Petey Sarron (1937)

This was Armstrong’s first world title victory, and right from the start, Henry became a living swarm of punches. The crowd yelled “They got Petey!” as Armstrong knocked out Sarron in the sixth round to everyone’s surprise. This would actually mark the beginning of his incredible run across multiple weight divisions.

Armstrong vs. Barney Ross (1938)

With the featherweight championship secured, it was time to go after the welterweight division title. This time, he’d face Barney Ross, an established champion that many believed could keep up with “Hurricane Henry” frenzied fighting style. To Barney’s credit, the fight went all the way to 15 rounds but the judges unanimously gave Armstrong the win and solidified his reputation as one of the best in the sport. He had already made history, but Henry was far from done.

Armstrong vs. Lou Ambers (1938)

Homicide Hank (as boxing experts started calling Armstrong) had his sights on the World Lightweight Title, held by Lou Ambers. Ambers was a particularly tough fighter with tremendous heart, and had thoroughly prepared himself to stop Armstrong in his title spree. Henry, on the other hand, was at a weight disadvantage but had tremendous spirit and blind faith in his skill and physical prowess.
By all accounts, the fight was brutal. The fight went the distance and the judges decided that Hurricane Henry narrowly took the victory, making him the only boxer to hold world titles in three different weight classes simultaneously. Remember that back then there were only eight weight classes, no junior or super distinctions to divisions, so he had to fight a wide range of powerful fighters for every title win.

Armstrong vs. Ceferino Garcia (1940)

Armstrong is known for simultaneously holding three division titles, but did you know that he almost took four?
Hurricane Henry actually challenged Garcia for the Middleweight title, an opponent he had already defeated during a welterweight title defense back in 1938. The fight was already shrouded in controversy before it even began, which was scheduled to last 10 rounds instead of 15, with the referee as the sole judge. Reportedly, Armstrong was even offered money to throw the fight during the 4th round.

Henry had tremendous love for the sport and to become the greatest that boxing had ever seen, so naturally he rejected what would’ve been a fortune so many years ago. He fought fiercely and true to his style, and according to all experts at the time, he had convincingly won the fight. The match ended at the 10th round and the referee gave the victory to Garcia, a decision that remains controversial even today. This was George Blake’s last assignment as a referee too, and many speculated he retired that day with a fat cash envelope to his name.

Today, we might be discussing how Armstrong took four of the eight division titles at one point during his career. I included this fight because, to many, he lost to dark interests that had tremendous sway and power over the sport at the time, not to Ceferino.
Armstrong’s style influenced countless fighters after him, but most understood that Henry had an unnatural stamina and strength that allowed him to keep such intensity for years. He was a legend in boxing history, and many experts actually rank him as the best pound-for-pound boxer of all time, due to his success across multiple weight classes.

Armstrong actually defended his Welterweight title 19 times during 1938 to 1940, so his dominance over the division was thoroughly prove, and beat other fighters even at a weight disadvantage, so it’s easy to understand their opinion.

#4 Harry Greb

Here’s another old-school name that deservedly takes the 4th spot in our list of the best boxers of all times. Harry was known as “The Pittsburgh Windmill” and fought from 1913 to 1926, a time when boxing had not evolved to even the playing field between fighters with different weights. This didn’t do Harry any favors, as he wasn’t a particularly tall or heavy guy, standing at 1.73 M and 74 kilograms, but it also didn’t stop him from beating heavyweights at times.

Harry fought light heavyweights, heavyweights and just about anyone that dared face him. The Pittsburgh Windmill threw punches from all angles at terrifying pace, something that’s known today as “volume punching” and aims to overwhelms opponents.

Greb fought and defeated 18 Hall of Famers during his career, which is absolutely insane. The kicker? At one point he suffered a nasty injury and was partially blind in one eye, and still managed to compete at the highest level. He was a human honey badger, small but incredibly fierce, tenacious and downright terrifying when he got his gloves on.

Let’s look at some of the fights that earned him a spot in our list.

Greb vs. Gene Tunney I (1922)

Gene Tunney wasn’t just another boxer: he was a heavyweight champion that defeated another boxing legend, Jack Dempsey. Greb wasn’t one to dodge opponents, and even though Gene was a heavyweight himself, his face was almost unrecognizable by the time Greb was done with him. The judges gave Harry the win by unanimous decision, simultaneously adding Tunney’s first and only loss in his otherwise perfect record.
Harry was absolutely fantastic during this fight. Imagine a much smaller boxer completely dominating a 1.83m heavyweight champion with a perfect record. It’s truly the stuff of legends.

Greb vs. Mickey Walker (1925)

Mickey Walker, known as the Toy Bulldog, was the reigning welterweight and middleweight champion, making him one of the few boxers to simultaneously hold two division titles. Greb didn’t hesitate and delivered a masterclass in volume punching onto Mickey, who in his defense, valiantly boxed and even turned the tides on Greb on some rounds.

The fight was a brutal back-and-forth, and the judges ruled it a draw, which was a very controversial ruling to say the least. Many believed Harry had won the fight, and this incredible display of strength only furthered his reputation as a ferocious boxer.

Greb vs. Mike Gibbons (1922)

Mike Gibbons was known as “The Phantom”, and was one of the most skilled boxers of his time, known for his defense and counterpunching. He was particularly feared because he’d sneak devastating counterpunches that would use your own strength, momentum and weight against you. Many believed that Greb’s style would suffer tremendously when faced with such a technical fighter.

However, Greb correctly understood the assignment and managed to outfight Gibbons. He stayed true to his style and applied relentless pressure and pain onto Gibbons, but he also managed to avoid his devastating counterpunches.

Greb vs. Johnny Wilson (1923)

Greb fought Wilson in 1923 for the Middleweight title, a southpaw that had a unique style that had earned him quite a reputation on the ring. Harry was fighting, by all accounts, a complete wildcard that could put a stop to his frenzied fighting style, but went on to relentlessly unload onto Wilson with all his strength. Wilson was unable to keep up and surrendered the title to Greb.

By the way, remember when I said that Harry had fought and won many of his fights while partially blind? Well, it turns out that he suffered an injury during a fight in 1921 which caused a retinal detachment in the right eye. This means that he was blind in the right eye, an injury he and his family kept secret so he could do what he loved the most: box.

It also means that this legend fought warriors outside of his weight category with one eye and still managed to win division titles. No other boxer has done that in the history of the sport, at least that we know of.

Also, keep in mind that Harry fought black fighters during a time when many others refused. Greb fervently believed in fighting any man that was capable of boxing, and paid absolutely no attention to the fighter’s circumstances, race or beliefs. This might come as a completely normal stance to have, but these were different times, and Harry never gave into the pressure of conforming and discriminating capable fighters.

The man was absolutely fearless and possessed technical skills, stamina and guts like no other, making him, hands down, one of the best boxers of all times.

#5 Manny Pacquiao

Manny Pacquiao is another living legend of boxing that started his career all the way back in 1995. He’s the only boxer in history to win world titles in 8 different weight classes, which is almost ridiculous to say out loud. He has completed from flyweight (112 pounds) all the way up to light middleweight (154 pounds) and dominated all eight weight classes as he did. The “PacMan”, as he’s fondly known in the box world is apart from nearly every other fighter in history, just because of this.

The PacMan has an explosive, aggressive, and incredibly dynamic style, a southpaw with lightning-fast hand speed and plenty of power behind every punch. Like many other great fighters on our list, he’s quick and unpredictable, which makes him a formidable opponent, as his record shows.

Pacquiao fought at an elite level for over two decades and is known for never dodging his opponents, which is a major feat in today’s highly commercial boxing. Let’s take a look at some of his most notable fights!

Pacquiao vs. Marco Antonio Barrera in 2003

This fight was Pacquiao’s breakout performance on the global stage, with many expecting an experienced champion such as Barrera to dispatch the Filipino warrior. However, the PacMan dominated from start to finish, knocking Barrera down twice before having to stop the fight in the 11th round. Manny had taken the world by storm and the featherweight division understood that a rising star was gunning for the title.

Pacquiao vs. Juan Manuel Márquez Series

These two titans fought a total of four times, and each fight was incredibly intense and brutal. They first fought back in 2004 (crazy to think it’s been 20 years!) and Pacquiao knocked Márquez down three times in the first round. Most people thought it was over, but Márquez rallied back to give us a memorable fight night. Manny took the next two fights by split decision, but in 2012 Márquez would have the last laugh and knock Manny out in the sixth round.
These fights are an integral part of Manny’s career, and his 3-1 dominance against such a talented fighter further cemented his rise in the boxing world.

Pacquiao vs. Oscar De La Hoya (2008)

De La Hoya was no joke: this man was bigger and more experienced than Manny, and most even went as far as calling the fight a modern David vs Goliath. Others were even angered at “mismatching” such a promising talent against a monster like Oscar De La Hoya. However, the PacMan would prove everyone wrong by dominating Oscar with tremendous speed and sharp combinations, until De La Hoya retired on his stool at the end of the eighth round.
This win catapulted Pacquiao to superstar status and proved he could compete with (and defeat) elite fighters in higher weight classes. He’d later snatch another record: most consecutive boxing world title fight victories at different weights at 15, between 2005 and 2011.

Pacquiao vs. Ricky Hatton (2009)

Hatton vs Pacquiao was one of the most hyped fights during that year, mainly because the British boxer held multiple world championships in the light-welterweight division, and one at welterweight. Manny, accustomed to being marked as an underdog, proceeded to knock Hatton twice in the first round, and then finished him off in the second round that put Hatton to sleep on the canvas. It’s crazy to think that such a capable fighter was still doubted due to his size, but then again, it might’ve all been a plot by the media to make sure those tickets were sold.

Pacquiao vs. Miguel Cotto (2009)

This is the fight that gave Pacquiao his seventh world title in a different weight class and established him as one of the greatest fighters of his era. Miguel Cotto was a naturally bigger and stronger opponent, but this fight proved, once again, you’d do well to look past physique stats if you want to analyze boxing like a pro. Manny dropped Cotto twice and systematically broke him down over 12 rounds before the fight was stopped in the final round.

Pacquiao vs. Floyd Mayweather Jr. (2015)

Fans of the PacMan probably won’t like that I’ve listed this fight too, but you’ll have to deal with it. Look, everyone knows that the fight, for most, simply didn’t live up to the unbelievable hype it got. But on paper it had everything: a master of defense and ring IQ against the boxing legend, one of the best pound-for-pound boxers the sport has ever seen. If anyone could break Mayweather’s perfect record, it was Manny.
Mayweather employed a defensive masterclass to neutralize Pacquiao’s offense, and many argue it started way before the date of the fight was even set. You see, many boxing experts and people in the know firmly believe that Floyd purposely dodged Manny while he was on his prime. Some say that they both avoided each other, but Pacquiao is not exactly known for doing such a thing.

Mayweather, on the other hand, has been accused in multiple occasions of cherry-picking his opponents to keep his immaculate record on zero losses. Even if that’s true, I still believe that Floyd Mayweather Jr. deserves a spot in a top 10 list of the best boxers of all times, he’s simply an incredible fighter that, simply said, can’t seem to lose.

I think I speak for all boxing fans that we’d loved to see a Pacquiao vs. Floyd Mayweather Jr. fight when Manny was still in his prime. I think it would’ve been a much closer battle, one that the PacMan might’ve taken early due to a crippling hit that would’ve left Floyd scrambling.

Final Words

Making a top 5 list of the best boxers of all times is always equally challenging and controversial. There are boxing fans that begrudgingly see some of the older names still topping the list, and I understand them wholeheartedly, but it’s important to respect and appreciate the sport’s history. Boxing, much like the world back then, was a much harsher place, where strength mattered more than ever due to its laxer rules and limitations, and that’s no small factor.

What all of these fighters have in common is that they all fought the best of their times, and many of the warriors in the opposite corner were hall of famers themselves. The quality of the opponent, the circumstances that led them to becoming the best and their raw talent and technical skills were fundamental parts of the criteria. Many of them became icons in their own right, but this had little to no impact when it came to placing them on their deserved spots.

Anyways, that’s one fan’s opinion, feel free to share your own with us!