Late 90s Ike wins by late stoppage. Holyfield SD in an extremely close fight if it's a prime Holyfield.
Nobody could stop Holy if he was anywhere near his best barring illness or injury I think Holy takes this, close decision in a brutal war that would live long in the memory
Holyfield Tko11 Ike, in a war. I think Holyfield's mental edge would carry the day for him in this one, as I always felt Ike was a McCall ( not crying, but just mentally losing it in the ring) waiting to happen.
Prime vs. prime, I see Holyfield grinding it out via UD. Ike has survived Tua's bombs and Evander has always been a hardy fighter. So I don't think anybody gets stopped, but I don't discount a few flash KDs.