Roy would have probably have to put on nearly a career best performance to pull it off at that point in time i think in my mind. So not impossible, but highly unlikely. Evander is not going to need a puncher's "chance" because he would land, and more than once.
Holyfield would run through him. Holy ain't no plodding one punch at a time bum Ruiz. Holy much like reed is a combo man and would tear roy up. Holy in 3.
There are more than one scenarios here how the fight go, but Evander wins in most of them. Jones wouldn't be able to make him passive the way he did to Ruiz The one question mark I have here is that Evander wasn't always at his best against small guys. His performance against Czyz was tame and Moorer gave him some trouble both times too. If Jones fought a perfect match he could win but the chances are not on his side
I actually lean towards Roy, I think Evander was pretty close to done at this point, had lost quite a bit of trigger speed and timing and I dont think his advantages in size and power are sufficient to overcome his deficits. Ie- he doesnt hit hard enough to do the job with cuffing or glancing blows and i think he'd struggle to land the clean ones he'd need. It'd be interesting tho, certainly no sure thing
I'd go Roy too. He made one of the dumbest moves in the history of boxing by going back down to 175. It was a mixture of dumbness and cowardice. After the Tarver KO he was officially mentally ruined as a fighter. He was celebrating going the distance with Tarver in his post fight interview after the third fight. If he'd stayed at heavyweight he could have been celebrating a UD against Holyfield in the post fight interview that night.