LONDON, England - In the first week of April 2016, Conor Benn was a touch over 140 pounds and his only boxing experience was 22 amateur bouts in various sports halls and ‘sheds’ in Sydney, Australia.

He was formally presented as Matchroom’s latest signing at a press conference at Trinity House, London on Tuesday, April 5 that year, four days out from his professional debut. The smiley teenager from that day is almost unrecognisable to the man who will face Chris Eubank on Saturday night in Tottenham.

Just three days earlier, on Easter Saturday 2016, Eubank had won the British middleweight title via the tragic 10th round stoppage of Nick Blackwell at Wembley Arena, during which the losing fighter had suffered a bleed on the brain. He would never box again.

The point is, 19-year-old Benn and 26-year-old Eubank operated in vastly different worlds back then. Given the difference in age, boxing experience and the 20 pounds which separated them in weight, the two paths did not look likely to cross in anyone's wildest dreams.

Even so, at that press conference on the banks of the river Thames, Eubank’s name was front and centre when the teenager left the top table for interviews with the small media gathering.

“I remember the questions that day,” Benn recalls, from his training base in Essex. “I just thought it was such a fantasy thing but everyone was still asking about us ever fighting.

“It was a big topic but I was like ‘I haven’t even had my first fight yet, give me a minute'.”

The nine-and-a-half years that have followed those embryonic stages of Benn’s career have not been smooth sailing and the path to Eubank was nearly blocked entirely when he returned adverse findings for the banned substance Clomifene in a pair of VADA tests before they were supposed to fight in October 2022.

It was suggested by his famous father Nigel that his son spent more than £1 million to ‘clear his name’ in the wake of those tests but it was not until November 2024 that a ruling from the National Anti-Doping Panel opened the door for him to fight in the UK again. They decided that they were not 'comfortably satisfied' that UKAD had proved Benn had committed an anti-doping rule violation for the use of clomifene.

Their first fight, in April, was worth the wait as the pair combined to produce a 12-round thriller which took both men to places they had never been as professional fighters. Three decades on from the second and final fight between their fathers at Old Trafford, the kids had lived up to the long-running rivalry with a classic at Tottenham Hotspur Stadium, which Eubank won on points.

On Saturday they will go again in the contracted rematch. Benn has already insisted he has no interest in a trilogy fight even if he levels the scores with a victory. His future lies back down at welterweight and he cannot wait to close the book on the Eubank rivalry.

So it is put to Benn, who is now the same age Eubank was when he beat Blackwell, that Saturday night represents the final fight ever between the two families. The dads first fought in 1990 but they had been initially linked in the late 1980s, meaning that a feud close to 40 years will come to an end on his watch. It is also, therefore, the last chance his family has of registering a win.

“I’m not thinking of it like that because I’m the one who has been in it,” he says. “But now you’ve deeped it, I will be thinking about this all week now. The pressure’s on.”

Although he is only half serious in his response, Benn knows that there is a lot riding on his reputation on Saturday night. Although the fight will take place two divisions above his natural weight, a second successive defeat to his bitter rival will be damaging to a career which was already put on hold due to the long-running Clomifene saga.

“I’m excited for the chapter to be over,” he says. “I’ve been talking about Chris since that first press conference before I’d even had a fight.

“I’m excited for it all to be over and I’ll never have to hear his name again, I’ll never have to think about him when I’m training. I can just move on and that’s it. I can say hello to him without any animosity or ill-feeling. Just ‘hey, Chris, you alright mate?’”

You sense that only victory in the rematch will truly allow him peace but Benn is confident he will get it right at the second time of asking. When asked specifically what needs adjustment ahead of Saturday night, his answer is succinct.

“My head fell off,” he says. “Rumour has it I’m still looking for it.

“My head fell off the moment the bell went to start the fight. I thought that there’s no coming back from this, I just had to get hold of him. I was sitting in the corner between rounds and had no idea about anything, whether I’d won the round or not, I wasn’t even thinking about that.”

Benn admits that the enormity of the event had got to him first time around and that contributed to his breathless but ultimately unsuccessful performance. He had cut an edgy figure on fight week too, curt in his answers and not much fun to be around for anyone.

As he speaks to The Ring a few days out from the rematch he is in a far more relaxed state of mind. He laughs and produces photos and videos of his young son Eli when asked how it has been training back at home in England following the decision to base the first camp in Majorca.

He was a kid back in 2016 when he made his debut, on a card which featured Matthew Macklin, George Groves and Lee Selby, not to mention Anthony Joshua’s second round knockout of Charles Martin which secured his first ever world heavyweight titles. He is a man now, with a wife, Victoria, and two young children, Eli and Idony.

“At home I’ve got an annex which we used as the camp house,” he says. “It’s on the same land but it’s away from the main house.

“But sometimes I’d go over there, go into the main house and it’s so peaceful. I’d see my two kids sitting there eating breakfast, Vic making coffee and I just think ‘this is what it’s for’. I watch them sitting there peacefully and I know that’s the reward. Job done, it’s like I’ve made it. I’ve cracked it.”

Incidentally, it was revealed this week that Eubank is also set to become a father for the first time as his partner is expecting twin boys. Although the suggestions have been made largely in jest, their arrival means that Eubank and Benn will now have sons around the same age. Perhaps Saturday night will not be the end of the Eubank-Benn story after all.

“Listen, Eli might say ‘yeah, I love it, I want some of that'. He probably will. If he does, he’ll have my full blessing and full support.

“But my job right now is to show up for my kids and that’s what all of this is about.”