Chris Eubank Jr. And Conor Benn will pen another chapter to their rivalry this weekend, just like their fathers did three decades ago.
Having traded on their family names during a long and tempestuous build-up to their initial encounter at a sold-out, Eubank Jr. Vs. Benn stood up on its own terms as a worthy stadium-filler.
Fans were enraptured at a sold-out Tottenham Hotspur Stadium in April, as the duo shared 12 thrilling middleweight rounds and Eubank emerged as the deserved winner in a competitive fight.
WATCH: Chris Eubank Jr. Vs. Conor Benn 2, live on DAZN
But for all their admittedly captivating qualities inside and outside of the ring, a sporting nation was not interested in the initial encounter because of Chris Eubank Jr. And Conor Benn.
The generation-defining exploits of their fathers in the 1990s made a deep impression on the collective British sporting psyche.
MORE: Chris Eubank Jr reveals what the deciding factors will be against Conor Benn
Who won Nigel Benn vs. Chris Eubank I?
During the thriving British middleweight scene at the turn of the 1980s and 1990s, Chris Eubank, Nigel Benn, and their contrasting personalities were on an inevitable collision course. Eubank, with his affected persona, jodhpurs, monocle, and preening disdain for boxing as a “mug’s game.” Benn, the former Royal Fusilier turned "Dark Destroyer" — a no-nonsense knockout artist who became a fan favourite.
A record of 22 consecutive knockouts at the start of his professional career shuddered to a halt when Benn faced Michael Watson in his first major domestic grudge match. Winging in with wild hooks from the opening bell, Benn ran out of steam and was picked apart by the more classically styled Watson. The end came when he was knocked down by a jab in the sixth round, utterly exhausted, and failed to beat the count.
Benn headed out to the United States to rebuild and reeled off five consecutive wins, claiming the then lightly regarded WBO middleweight title against Doug de Witt before stopping Thomas Hearns’ former conqueror Iran Barkley inside a round. He returned home in triumph in November 1990 to face the undefeated and outspoken Eubank, by then 24-0 but without a comparable victory on his record.
Accompanied in the ring at Birmingham's NEC by Richard Steele in November 1990, the man who oversaw the chaotic mayhem and brutality of Hearns' 1985 bout with Marvin Hagler, the two produced a bout at times worthy of comparison in terms of intensity and violence.
Benn forced Eubank to take a count in the eighth round. The challenger protested that he'd slipped, but his left eye was swollen shut. Eubank's relatively more measured and slicker boxing reaped rewards despite him having to fight through a badly cut tongue.
The end came in the closing seconds of round nine after Eubank crashed a right into Benn's jaw. His legs stiffened, and Eubank laid on punishment in the corner. Benn managed to stagger back to centre ring, but when he absorbed Eubank's follow-up assault, Steele decided he had seen enough and jumped in to spare the battered champion.
WATCH: Chris Eubank Jr. Vs. Conor Benn 2, live on DAZN
Who won Chris Eubank vs. Nigel Benn II?
Junior and Conor might have settled terms relatively quickly on an immediate and lucrative rematch. The path to fight two for their fathers took a few more twists and turns.
Benn gradually rebuilt from that bruising reverse with six consecutive wins, but, as was the case after the Watson loss, salvation came on the road when he travelled to Italy, and WBC super middleweight champion Mauro Galvano retired due to a gashed eyebrow after three rounds.
Eubank also moved up to 168lbs for a rematch with Watson, against whom he won a contested points verdict in the final defence of his middleweight title in June 1991. The contest for the vacant WBO super middleweight crown three months later ended in tragedy, with Eubank dramatically coming from behind to secure a stoppage victory in the final round, and Watson suffered severe and life-altering injuries.
A succession of perhaps understandably tepid encounters followed, with Eubank defending the belt he won on that fateful night seven times over the course of two years. It meant Benn once again felt like the fighter with momentum, heading into their blockbuster rematch in front of 40,000 fans at Old Trafford in October 1993.
It was a more tactical affair the second time, with sporadic bursts of gripping action. In the sixth round, Benn was docked a point for persistent low blows, a moment that would prove crucial in the final outcome. Judge Harry Gibbs scored it 115-113 to Eubank, Carol Castellano awarded it 114-113 to Benn, and Chuck Hassett had it 114-114 even, meaning a split decision draw.
Did Nigel Benn and Chris Eubank fight a third time?
Despite the understandable clamour for a trilogy, a third fight did not materialise. Eubank took a lucrative television deal with Sky Sports, meaning ITV and Benn did not figure in his plans. After several close shaves on the scorecards, he finally lost his WBO crown to Irishman Steve Collins in March 1995. In the rematch six months later, Eubank was on the wrong end of a split decision.
Collins also inflicted a pair of defeats upon Benn the following year, losses that would prove to be the last acts of a superb career. Arguably, the finest win on his record came in 1995, although Benn’s fearless and ferocious triumph over the formidable American puncher Gerald McClellan came with similarly horrific consequences to Eubank’s rally against Watson.
Eubank retired after a torch-passing moment in defeat to Joe Calzaghe, who won his old vacant WBO strap, and a pair of gallant attempts to win the WBO cruiserweight title from Carl Thompson came up short.
He and Benn had a third encounter of sorts. It was a bizarre British TV spectacle where they trained as Roman warriors and duelled in an ancient amphitheatre. Plenty of the old animosity seemed to remain. "Only you can do this to me, you know that, don't you?" Benn said to Eubank in an aggressive yet somehow affectionate embrace after the pair had previously almost come to blows.
In 2018, with both men in their 50s, The Sun reported that negotiations had been taking place for a third fight, tapping into the modern trend of former favourites getting back into the ring for one last hurrah.
Those came to nought, but both men were in the ring and at ringside as their sons took centre-stage, Eubank in 2025 dramatically ending his estrangement from his son to enter the stadium side-by-side with him. The elder Eubank had lost none of his flair for a showbiz flourish and - contrary to many expectations - the fighting names of both families emerged enhanced.