UD Leonard. Quite like the hagler vs Leonard fight, but eubank was pretty limited on the front foot. He didn't really like going foward, also he took too many rounds off. Leonard would shoeshine his way to a decision.
It depends on where the fight is held. In the US Eubank would have to KO Leonard to win, as the judges would be impressed with all his show boating whilst actually doing nothing. Leonard can't KO Eubank in a million years, though the reverse is more than possible, so anywhere outside Murica where Leonard would be forced to help make the fight suits Eubank who liked guys coming to him, to set up his big right hand counters.
Some people here will say eubank couldn't ko Leonard. But he's proven before if he times you right, he can end the fight.
Leonard wins because he wins the mental game: that was, in addition to his great physical gifts, his true strong point. He got the better of everyone apart from Duran the first time, at least until the very end when he was past it. Eubank wasn't mentally strong in any way. This is a guy who fell apart because Steve Collins, a pedestrian fighter, made up a story about being hypnotised to not feel punches. Eubank literally freaked. So it looks like a complete mismatch mentally to me. I have to laugh at the post about Leonad showboating ... in England they gave Eubank points for posing. He would stand stock still in the ring like a maniquin and fans would rise to their feet to cheer. Or stare after the bell and they'd go nuts. Never quite understood his appeal. I do think he was somewhat gifted, but much of his stuff was smoke and mirrors ... I mean, he goes to the wire to get a razor-close decision over the likes of Tony Thornton, a full-time postal worker and part-time boxer; another close win over Sugar Boy Malinga -- a year later James Toney practically shuts Sugar out, and a young Roy Jones Jr. whacks him out with ease. Leonard had substance. Much of Eubanks' career was at 168, not 160 ... but he was only 5-10, so at middleweight not a really imposing size advantage.
Leonard by comfortable decision. His mental edge alone would be enough. Add to the equation his forcing Eubank onto the front foot where he's uncomfortable. Ray would n't hurt him,though,as Chris had a rock solid chin.
Leonard UD with Eubank having his moments maybe even dropping Leonard but Ray would outbox him in due course.
I'm not stating that Chris would definitely KO Leonard, but he would certainly drop him easily enough, and make him think twice about getting another one. But as stated Leonard could hit Eubank with the best punch he ever threw, and nothing would happen except for Chris adopting one of his body builder type poses and shaking his head at Leonard.
Luckily for leonard I think had the handspeed and foot speed to avoid the counter, because if ate them flush he would be dropped. And Leonard would need a sledgehammer to knock down eubank, not happening. Give me benn vs leonard instead.
Yeah, that would be better, because Leonard could actually hurt Benn. That said Benn was actually at his most destructive when badly hurt himself. Plus he definitely puts Leonard to sleep with one shot if it lands. I see Leonard happy to comfortably out box Benn in even better fashion than Mike Watson did, and not getting involved in anything more than that, but I see him losing to Eubank, due to being too wary of his power, and unorthodox style.