You don’t see moments like this every day. Boxing fans are in for a special moment as the sons of Chris Eubank Sr. and Nigel Benn will step into the ring in a few hours to finish what their fathers started 35 years ago. Their rivalry was one of the most intense in British boxing, full of bad blood and unfinished business. Now, their sons are writing the final chapter in front of 62,000 fans at Tottenham Hotspur Stadium on April 26th.

Though Mike Tyson questioned the fight’s appeal, the viral “egg” incident turned all eyes toward it. Still, drama surrounds the event. Chris Eubank Sr. has publicly called the fight “illegal” due to the weight difference. But will that stop the fight from happening? Nope. Now, as fight night approaches, fans are left wondering: Will Chris Eubank Sr. show up after all? And have Chris Eubank Jr. and Conor Benn found common ground beyond the rivalry that began with their fathers?

Chris Eubank Sr. and Nigel Benn boxing rivalry: Who won?

The rivalry between Chris Eubank Sr. and Nigel Benn is one of British boxing’s most legendary—and most bitter. Their first showdown in 1990 wasn’t just a fight, it was a collision of pride, ego, and raw emotion. After years of trading insults and circling each other in the middleweight and super middleweight scenes, they finally stepped into the ring for the first time in 1990 for Benn’s WBO middleweight title. Tensions were sky-high. Benn Sr. even tried to mess with Chris Eubank Sr.’s ring walk, setting the tone for the chaos that followed.

The bout itself was an all-out war. By the fifth round, Chris Eubank Sr.’s tongue was badly gashed and bleeding. And Benn Sr., on the other hand? He was gassed out, too. Nigel Benn’s eye was swollen shut. But still, the 45-5 boxer dug deep and stopped Benn with a brutal combination in the ninth. It was a clean TKO win, but the feud was far from finished.

Three years later, they met again. This time in the super middleweight division, both were world champions (Eubank was WBO and Benn had the WBC belt), and 45,000 fans packed Old Trafford hoping for a sequel worthy of the hype. The stakes were even higher, with a shot at promoter Don King’s stable and unified glory on the line. But lightning didn’t strike twice. The rematch was tense but lacked the fireworks of the first fight. And when the final bell rang, the judges couldn’t separate them. It ended in a split draw, and the trilogy that fans dreamed of never came to pass.

Still, despite the unfinished business, their rivalry left a permanent mark on the sport. And now, over three decades later, it’s their sons stepping up to finish the story their fathers never got to complete.

Chris Eubank Sr. and Nigel Benn engage in a brawl on TV

Back in the day, if there was one rivalry in British boxing that truly had fans on the edge of their seats, it was Chris Eubank Sr. vs. Nigel Benn. So when 18 million people tuned in to watch their rematch in 1993, a trilogy felt like a done deal. But it never happened. Why? As Benn once put it, “We spent three bloody years talking, but Chris is impossible.”

Then came 2003. A decade after their rematch, Channel 5 stepped in with a different kind of third act—“Gladiator: Benn v Eubank.” Set in Rome, this wild reality TV concept had the two legends trading boxing gloves for ancient weapons, training under the blazing Italian sun at a gladiator camp in Ostia Antica. They were even given new names: Eubank became “Maximo”, Benn was “Eracido”. Strange choice, since the whole point was to pit two of boxing’s most famous names against each other—and then they… renamed them. But weird names aside, the drama was real!

From push-up punishments to shield challenges, the two men clashed at every step. Anyway, things reached a boiling point on Day 2 during the “Defend Your Enemy” challenge, where both were chained together and had to guard each other’s backs. Eubank won, then took a jab—verbally—at Benn’s character. “He’s only interested in looking after himself, that’s my observation,” he said, adding, “No disrespect,” which, of course meant total disrespect. Benn didn’t take it lightly. So what did he do?

Nigel Benn shoved Chris Eubank hard and nearly triggering an all-out brawl. Even when Eubank offered a handshake, it was just a setup to push Benn back. Classic chaos!

But leaving the show and the chaos aside, what surprised fans most wasn’t the fights or the fire. It was the friendship. Between the insults and challenges, there were moments of genuine connection: hugs, handshakes, even a few kind words. Benn summed it up perfectly at the end: “Me and Chris, we have a long history together, both being world champions–and it was great to meet him again.”

Was it ridiculous? Sure. Entertaining? Absolutely. And somehow, it became a fitting, if unconventional, final chapter to one of boxing’s greatest rivalries.

Rivalry between Chris Eubank & Nigel Benn takes an unexpected turn

This Saturday night, the iconic family rivalry gets its next chapter with the Conor Benn vs. Chris Eubank Jr fight. And while the sons are set to battle under the lights, all eyes are also on the stands… because this could be more than just a fight—it could be a reunion.

Nigel Benn, now 61, is confirmed to be ringside, ready to watch his son carry on the legacy against the son of his old nemesis. But noticeably absent? Chris Eubank Sr. Despite being just 58, and once a constant presence in his son’s corner, Eubank Sr. hasn’t been by Chris Jr.’s side since 2019. Their estrangement stems from something deeply personal—Jr.’s need to carve his own path.

In a recent interview on Piers Morgan Uncensored, Eubank Jr. explained, “It got to a stage where I needed to step out of the shadow completely. It’s a big shadow.” He went on to say that while Nigel Benn let his son sink or swim on his own, Eubank Sr. was always right there, and eventually, that presence felt suffocating. “I needed to walk my own path. He [Chris Eubank Sr.] was not happy with that decision.”

And yet, despite all of it, Nigel Benn is hoping for a reconciliation. Speaking emotionally to the BBC, he made a heartfelt plea: “I just wish Chris [Eubank Snr] was there. Because it is like a family affair, and I just hope they patch it up.” Benn didn’t hold back, calling on his former rival to show up for the bigger picture, not the fight, but the family. “At the end of the day, I don’t want him having a disagreement with his son. A son that he loves. A son that he cares for.”

He continued with a touching invitation: “If you are watching Chris, come and support your boy mate. We all want you there, so we can see each other after the fight and hug each other and say it is all over.”

This weekend, it’s not just about punches and pride. It’s about legacy, growth, and maybe even forgiveness. Will Chris Eubank Sr. show up? What do you think?