Chris Eubank announced his retirement from the ring in October 1995. He made a quick comeback in 1996, however, defeating Luis Dionisio Barrera and Camilo Alarcon. After Steve Collins withdrew from his WBO super-middleweight title defence against Joe Calzaghe and unexpectedly retired in October 1997, Calzaghe was matched against Eubank for the vacant title with eleven days notice. Eubank had been scheduled to box at light-heavyweight on the undercard. Eubank was knocked down twice and lost on points to Calzaghe, but saw his popularity rise as a result of managing to finish the fight against his more fancied opponent. Eubank then added
Nigel Benn vs. Chris Eubank his WBC belt, Eubank his WBO championship. Astonishingly, Don King had not written the event of a draw into the contract, and as a result neither fighter was contractually bound to join him. The pair never fought again, despite a £6 million bout at Wembley stadium being touted for Eubank's eight fight Sky deal. Benn faced Gerald McClellan, pound-for-pound one of the most devastating fighters of the 90s, and his career paralleled Eubank's when McClellan was paralysed as a result of this bout. Benn was finished mentally and almost physically after this violent war, and lost first his title then