The Chris Eubank Vs Nigel Benn rivalry remains one of the most iconic feuds in British boxing history – but how many times did they fight, and who won?
Two names that have woven themselves into the fabric of British boxing, the Eubank and Benn families have battled in the ring across multiple generations.
This weekend, Chris Eubank Jr Vs Conor Benn 2 takes place at the Tottenham Hotspur Stadium in London.
But it was their fathers, Chris Sr and Nigel Benn, that started this famous rivalry.
Their meetings were legendary, and sparked a decades-long grudge as contrasting styles and personalities clashed.
But how often did they actually face each other?
How Many Times Did Chris Eubank Sr Fight Nigel Benn?
Chris Eubank Sr and Nigel Benn fought twice during their professional careers.
Their rivalry was a defining aspect of British boxing in the 1990s.
ICONIC FOUR MAN FACE OFF
THE EUBANK'S VS THE BENN'S
🔥🔥🔥🔥#EubankBenn2 pic.twitter.com/DmvbRENCPE
— Matchroom Boxing (@MatchroomBoxing) November 13, 2025
Their first encounter took place in November of 1990, in a much-anticipated WBO middleweight title fight.
Benn, known as a destructive puncher, took on the unbeaten Eubank, who boasted supreme technical ability.
The collision of different personalities and fighting styles helped build the fight into what it became.
It would take three years before Eubank and Benn would have their rematch.
Billed as “Judgement Day”, the super-middleweight bout saw both fighters enter the ring as world champions, in one of the most-watched fights in British TV history.
But despite the hype and spectacle of their first two fights, the pair would never meet in the ring to complete the trilogy.
Interest in the family rivalry may be declining, though, with Chris Eubank Jr Vs Conor Benn ticket sales struggling ahead of their rematch.
Who Won When Chris Eubank Sr Fought Benn Sr?
Over the course of their two legendary bouts, there was little to separate the pair.
However, the first fight did produce a winner.
Fight 1 – November 1990: Eubank Wins
In their first contest, Chris Eubank Sr defeated Nigel Benn via ninth-round TKO.
During a brutal war of attrition, Benn controlled the early rounds with his incredible power.
But Eubank’s unbreakable chin, expert precision and patience eventually won out.
The referee stepped in during the ninth round, declaring Eubank the WBO middleweight champion.
That victory helped propel Eubank Sr to stardom, with Benn vowing to get revenge.
Fight 2 – October 1993: A Controversial Draw
Three years later, the two would meet again, this time for the WBC and WBO super-middleweight titles.
The rematch ended in a split draw, with neither fighter victorious.
Once again, Benn’s aggression and work rate met Eubank’s accuracy and technique.
The judges were divided, with one scoring in favour of Benn, one for Eubank, and one calling it a draw.
But many fans believed Benn had done enough for the win, while others argued Eubank deserved the draw.
The result remains a controversial one to this day.
What Happened After Chris Eubank Sr Fought Nigel Benn?
After their second meeting, both fighters enjoyed further success.
But despite public demand and huge financial incentives, a trilogy never materialised.
Eubank later claimed he had no wish to fight Benn again, citing the huge mental and physical toll of their brutal second fight.
Benn, meanwhile, was keen for a third bout, but it never happened.
ONE DAY LEFT‼️
Chris Eubank Jr and Conor Benn settle unfinished business in their rematch, tomorrow night at Tottenham Hotspur Stadium in London 💥
The Ring: Unfinished Business l Exclusively on DAZN l Nov 15th 🥊 pic.twitter.com/vXLvWgeLJL
— Ring Magazine (@ringmagazine) November 14, 2025
In the years that followed, Eubank Sr became one of Britain’s most recognisable sporting stars.
He went unbeaten in his first 43 professional fights, eventually losing the super-middleweight title to Steve Collins in 1995.
Benn’s record was 37-2-1 after the second Eubank fight, with him also going on to lose to Collins at the end of his career, retiring after back-to-back defeats in 1996.
The Eubank Vs Benn feud now lives on through their sons, with Chris Jr and Conor Benn set for their second bout this weekend.
