One of Britain’s greatest boxing rivalries was well and truly alive in the 1990s, as Chris Eubank and Nigel Benn had a fantastic series of fights.
Meeting for the first time in November 1990, Eubank would put his undefeated record (24-0) on the line as he challenged Benn (27-1) for his WBO World Middleweight title.
The two would meet in Birmingham, England, as Benn was looking to make his second defense of the title.
Although the fight was closely contested throughout eight rounds, the ninth would see Eubank earn a stoppage victory, with a standing TKO loss for Benn.
However, their second meeting had a less conclusive finish.

Chris Eubank vs Nigel Benn II took place in Old Trafford
Despite their first fight being closely contested, rivals Eubank and Benn would not meet again for another three years. Eubank and Benn even signed the contract for the rematch on live television.
For their sequel bout, Eubank and Benn would face one another at Old Trafford Stadium, home to Manchester United Football Club.
Meeting in October 1993, the two would rematch in a world super-middleweight unification fight. Eubank’s WBO title was on the line, while Benn was the WBC champion of the division.
However, neither man would lose their belts in Manchester that night.
After 12 rounds, the bout went to the judge’s scorecards, where the bout was a split draw. However, many people feel as if Benn was the winner of the fight.
Speaking on ‘I’m a Celebrity… Get Me Out of Here!’ Eubank said that if it wasn’t for his opponent being deducted a point for a low blow, Benn would have won the fight.
However, the fight was officially declared a draw, meaning both men retained their titles.
Why did Chris Eubank and Nigel Benn never have a trilogy bout?
Despite the controversial ending to their second meeting, Eubank and Benn would both retire before settling their series with a third fight.
Although Eubank called out Benn in 2015, they were long beyond their fighting careers at that stage.
In terms of why the third fight didn’t happen, boxing promoter Barry Hearn gave his opinion to Rob Moore.
Hearn said that his immediate thoughts after the fight was announced a draw was that Eubank and Benn would meet for a third time.
However, Hearn revealed that, ultimately, pre-fight contractual agreements with fellow promoter Don King would be the reason that a rubber match did not happen.
King expressed interest in both fighters prior to their sequel bout, however, the fight result would cause complications in his and Hearn’s agreements.
Following the result, Benn would sign with King, moving on from working with Hearn.
Hearn then implied that although Eubank was still working with him, Benn working with King would cause complications in a trilogy bout.
Eubank and Benn’s sons will, however, have a fight in 2025, which can be seen as a trilogy bout between the two families. Chris Eubank Jr. and Conor Benn will face each other in London, in April 2025.