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
Chris Eubank 20 lbs in weight and challenged Britain's Carl Thompson for the WBO cruiserweight title. Eubank floored Thompson in the fourth round but, as in the first Steve Collins fight, failed to press home his advantage. The fight went the distance, with Thompson's strength and durability eventually telling in the later rounds. Thompson won by unanimous decision, but the closeness of the fight was reflected in the scoring, with two of the three judges giving the fight to Thompson by a single point. A rematch was quickly arranged for three months later and they again fought for the WBO cruiserweight championship