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 a regular customer, started designing tailored suits for Cad and the Dandy, a Savile Row bespoke tailoring company. On 19 August 2015, a spoof trailer was made available for "Youth Hostelling with Chris Eubank" in association with Hostelworld, detailing Eubank's journey around Britain in an effort to learn more about youth hostels. The joke originates from the comedy show "I'm Alan Partridge", in which the title character pitches a selection of ideas for television shows. Eubank and his first wife, Karron (married on 23 December 1990 in Brighton), had four children (Christopher, born on 18 September 1989; Sebastian, born on