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 twice more to Steve Collins, who magnanimously claimed afterwards that Benn was the greatest British boxer ever, and wished he could have fought him at his prime. Eubank too lost his title and unbeaten record, also to Collins by a split decision. He retired, and came out of retirement to face a young Joe Calzaghe, who beat him on points. He fought for the WBO cruiserweight title, losing another split decision to Carl Thompson, and the rematch when, ahead on points, the doctor stopped the fight due to Eubank's swollen eye. This time, he retired for good. Two legends of