Reflecting on the rivalry between the Eubank and Benn families ahead of Tottenham clash

As the boxing world counts down to April 26, 2025, when Chris Eubank Jr and Conor Benn finally face off at Tottenham Hotspur Stadium, the significance of this long-awaited grudge match extends far beyond the ropes and the fate of the middleweight division.

This isn't merely a contest between two elite fighters – it's the continuation of British boxing's most storied family feud, a rivalry that has simmered and boiled for over three decades.

With 60,000 fans expected to fill the state-of-the-art north London venue, the bout represents not just the culmination of years of build-up, but also the rekindling of a rivalry that defined an era of British boxing.

The fierce animosity, dramatic postponements, and theatrical press conferences have only fuelled public fascination with a story that began long before either man stepped into a professional ring.

While the IBO Middleweight champion has spoken about both Nigel and Conor, and he slightly edges the Conor Benn vs Eubank Jr odds, he will need to back up his words after claiming Conor has damaged the family name.

“His father's upset more than him because he's destroyed his father's legacy,” he said. “He's put a black mark against the Benn name.

“The worst thing Conor's done is put question marks against the Benn name, because as they say "like father, like so. So if he's capable of cheating, did his father cheat? That's now the question that arises. I don't believe his father didn't know what he was doing. I just don't believe it.”

The rivalry stretches back decades between the families. The seeds of this generational conflict were planted in the early 1990s, when two contrasting personalities captured the imagination of the British public in a way few sporting rivalries ever have. Their two legendary encounters still resonate through boxing history, casting long shadows that their sons now step into.

Their first meeting in 1990 was a brutal affair, fought for Benn’s WBO middleweight title. In front of a raucous crowd at Birmingham’s NEC Arena, both men traded thunderous shots in a back-and-forth contest that is still remembered as one of the greats. Eubank emerged victorious, stopping Benn in the ninth round to claim the title and bragging rights.

Three years later, the pair met again—this time as super middleweights, with both holding world titles. Old Trafford played host to the rematch, with 42,000 fans in attendance and millions more watching at home. The bout ended in a controversial split draw. Neither man had done enough to clearly take the win, and a trilogy fight—heavily demanded by fans—never materialised.

The rivalry, as a result, was left unresolved to the frustration of the fighters as well as fans makingboxing bets. And in many ways, that tension never truly went away.

Fast forward 30 years, and the story continues. Conor and Eubank Jr have carried the weight of that rivalry into a new generation. They’ve grown up with it, lived in its shadow, and now—finally—they’ll have the chance to settle it in the ring.

Their original bout was scheduled for October 2022 and promised to bring full-circle closure to a feud that had gripped fans since the 90s. But just days before the fight, Benn failed a drug test and the event was pulled, sparking a media storm and lengthy legal battle with the UK Anti-Doping Agency.

While Benn maintained his innocence and was eventually cleared to fight again, the delay meant the bout was shelved for nearly two years—adding yet more tension, frustration, and headlines to a fight already laced with history.

Now, the stage is set once more. The Tottenham Hotspur Stadium will play host to the long-delayed contest, with an expected crowd of over 60,000. While it may not rival Wembley for Anthony Joshua vs Daniel Dubois, it’s shaping up to be one of the biggest British boxing nights of the year—and one of the most emotionally charged.