BoxRec

Holyfield is still a little green and was pushed hard by Dwight.

Dempsey showed killer instinct in that fight.

How do you see this one going?

I think Holyfield's overall better craft and amateur pedigree would've been enough to eventually beat Dempsey by Boxing. It would be a back and forth evenly matched fight whenever Evander tried to slug it out with Jack.

I'd take Evander.

i still hold the view that dempsey's way of
boxing would not hold up against a prime
modern ATG. evander could take a punch,
and his (in my view) better coordination
between offense and defense would come
into play rather sooner than later.

In their primes, this would probably have been a terrific fight. However, Holyfield had yet to reach his prime. I would have to go with Dempsey here.