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The Grueling Truth - Where Legends Speak / Latest Boxing News & Rumors Today / Boxing History / Who was Joe Calzaghe’s most difficult opponent? The answer might surprise you

Who was Joe Calzaghe’s most difficult opponent? The answer might surprise you

Publish Date: 03/06/2026
Fact checked by: Mike Goodpaster
Nov 8, 2008; New York, NY, USA; Joe Calzaghe and Roy Jones Jr. trade punches during their 12 round light heavyweight championship fight at Madison Square Garden. Calzaghe defeated Jones via unanimous decision. Mandatory Credit: Ed Mulholland-USA TODAY Sports

Joe Calzaghe engaged in 46 professional fights. He knocked out 34 opponents – and never lost.

There were some tough fights along the way.

Let’s take a look.

Calzaghe fought former champion Robin Reid on February 13, 1999, in Newcastle, England. Reid was 28 and hungry again. He’d lost his super middleweight title in 1998 to underdog Thulani Malinga. Reid wanted it back.

Calzaghe was making his fourth defense of his WBO strap.

Reid was several inches shorter than Calzaghe. But what he gave up, he made up for with strength.

Reid had knocked out 20 of his 28 opponents. Calzaghe was favored, but when the two squared off, the grittiness of the challenger surprised many.

Calzaghe was his usual frenetic self, bouncing punches off Reid’s head easily, but Reid’s return fire caught the eye of many. The challenger’s right, often a southpaw’s nightmare, caused issues for Calzaghe. He took the shots well, but ate far too many for his liking.

The fight went the limit (12 rounds) but wasn’t unanimous. One judge scored it 116-111 for Reid; two others had Calzaghe winning by the identical tally. Calzaghe had outworked and outlanded Reid, but the tough man, nicknamed “Grim Reaper,” – had made Calzaghe work.

To this day, Reid feels the decision was unjust.

“I have studied a tape of it,” Reid told Doghouseboxing. “And I seriously believe I won that fight by at least two rounds.”

Calzaghe made his debut in America by fighting champion Bernard Hopkins in 2008.

Hopkins had turned the fight racial by quipping, “I’ll never let a white boy beat me. Never.” Hopkins’ words did not bother Calzaghe, the white Italian boy from Wales.

Calzaghe had held a part of the super middleweight belt for 11 years, defending it 21 times. Hopkins had defended his middleweight title 20 times before losing it to Jermaine Taylor.

Hopkins moved up to the light heavyweight division in 2007 and captured The RingĀ light heavyweight title.

Calzaghe entered the ring, a 3-1 favorite. A minute into the fight, Calzaghe found himself on the seat of his pants, courtesy of a Hopkins lead right hand. Calzaghe got up quickly, with a cut on the bridge of his nose.

Hopkins continued to do well in the early going until Calzaghe began to pressure Hopkins relentlessly. The tactic worked. Calzaghe found his groove and outworked Hopkins the rest of the way. The fight was hardly a classic, with lots of grappling.

Two judges saw the fight for Calzaghe – the other for Hopkins.

Hopkins disagreed with the decision.

“I just really feel like I took the guy to school,” he said after the fight. “I feel like I made him fight my fight, not his.”

Calzaghe saw the fight differently.

“He was so awkward. It wasn’t pretty, but I won the fight.”

Calzaghe went home to Wales in 2007 and fought WBC and WBA super middleweight champion Mikkel Kessler before 50,000 adoring fans.

Denmark’s Kessler was a rugged and determined fighter. He was undefeated in 39 bouts – scoring 29 knockouts. Calzaghe was 43-0.

Something had to give, and for four rounds, neither boxer did. The mood was tense as the fighters threw hands. Calzaghe felt Kessler’s power.

“He caught me with some good shots early on, especially in the fourth round, which maybe made me focus a bitĀ better,” Calzaghe told Nick Parkinson of ESPN.com in 2017.

Focus, he did.

Calzaghe used his speed and boxing skills – combining an assortment of jolting blows, tight defense, and a firm chin.

Said Kessler after the fight.

“His punches weren’t particularly hard, but it was confusing when he hit you 20 times.”

This time, the decision was hardly in doubt.

“It was the fight of my life,” Calzaghe said. “Mikkel Kessler topped it, winning all the belts and fighting in front of all those fans in my hometown.”

But was it his toughest fight?

Not according to Calzaghe.

ā€œI’ve never been so exhausted, and I’ve never been asked so many questions,” remembered Calzaghe to boxingnewsonline.net last year “I know my will and hunger were the only things that got me to the bell that night, and I know I was completely running on empty for the last couple of rounds.”

So, what fight is Calzaghe referring to?

Chris Eubank Sr. was 31 when he fought Calzaghe. He was a two-time champion and never lacked confidence. Calzaghe was 25, undefeated in 22 fights. He flashed fast hands and feet – even displaying power.

His ego was healthy as well.

“I was knocking everybody out in the first couple of rounds, so I was a bit cocky and brash,” said Calzaghe.

Seconds into the fight, Calzaghe thought it was over after flooring Eubank Sr.

“After I dropped him in the first 15 seconds, I got excited and thought it was going to be easy,ā€

Eubank was stunned as well.

ā€œI came out of the corner for round one smiling,ā€ Eubank said. ā€œI was moving around and sizing up the terrain when ā€˜Boom!’ Calzaghe hit me with a huge shot that came out of nowhere and knocked me down. A first-round knockdown had never happened to me in my entire career.”

Eubank congratulated Calzaghe on knocking him down.

Calzaghe spent the rest of the round trying to finish Eubank. It didn’t happen. A few rounds later, he was exhausted. Eubank went to the body. The blows hurt. All the nervous energy was gone.

Eubank fought hard, but Calzaghe fought better. He dug down deep and stayed a step ahead. Calzaghe scored a flash knockdown in round 10.

Eubank rose quickly and furiously, pleading his case.

He was also desperate.

Calzaghe was way up the scorecards – still, he tried to knock out Eubank in the 12th and final round. Eubank countered, but couldn’t land the big one.

Eubank had taken Calzaghe to a dark place, but he had climbed back to the light and won the bout.

“That was by far my hardest ever fight,ā€ said Calzaghe.

Ā 

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