I'm putting a vote out for Eubank. These types of match-ups are difficult for a number of reasons, (but I started this thing, might as well finish it) lack of footage first and foremost. Dempsey was considered unbeatable in the late 1800's...generally weighing around the welterweight limit he fought bravely against one of the most brutal and legendary punchers in Bob Fitzsimmons...After being knockdown in the neighborhood of nine times, Fitzsimmons begged Dempsey to give up and not receive any more punishment...through bloody, and smashed lips, Dempsey told Fitzsimmons, "You will have to knock me out, I'm not quiting." Fitzsimmons did KO Dempsey...But he had his utmost respect as a fighter. That being said...I'll take Chris Eubank to win by mid round KO...But I'm not doing Dempsey justice...because I don't know his true attributes as a fighter...The heart is certainly there.
I always go with the fighter who is more adjusted to the rules used in those match up and in this case it´s Eubank. Having said this, I think Dempsey is the far greater and better fighter.