1. Holyfield vs. Frazier I can see Holyfield's superb later movement, boxing and occasional brawling actually paying off in a very late stoppage in a very competitive fight. 2. Trinidad vs. Hagler Tito's power and underrated durability depsite the potential for early KD's will see him to the late rounds where he'd inevitably be behind and discover that Hagler is too big, too strong, and too skilled. This fight would never see the cards, but I do believe it'll see the late rounds.
I don't think Cotto would last more than a couple of rounds against the Duran of Montreal. Referee or corner stoppage with Miguel in a hell of a state saves him from the imminent KO blow.