Chris Eubank recognisable celebrities of the period. In his final two years of boxing he challenged then-up and coming contender Joe Calzaghe in a bid to reclaim his WBO super-middleweight title, with a victorious Calzaghe later claiming that it was the toughest fight of his whole career. Eubank's last two fights were against WBO junior-heavyweight champion Carl Thompson, both of which were brutal encounters. In the rematch, Eubank was stopped for the first and only time in his career. Eubank is credited for his bravery in the ring, in which he was able to take considerable amounts of punishment from power punchers
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