So what kind of results would Mike achieve if he fought against Holyfield's opponents (at the time when Evander fought against them)?
Tyson at his best I believe is the strongest H2H fighter and should be favoured against Bowe and Lewis. It’s difficult to say how good Tyson was when he wasn’t 100% though. Holyfield even as a waaaaay slowed down fighter at 36/37 had 2 close ones with Lewis, whereas an old Tyson got demolished by that same opponent. A Tyson not firing on all cylinders is supposedly not much good and would probably be smacked to pieces by Bowe and Lewis, would be in major trouble against Mercer and might be a 50/50 against old Foreman.
He beats them all with Bowe, Lewis, being the toughest match ups he could lose. He also has much easier time vs the likes an old Holmes, Moorer, etc. But surprisingly may find Big George troublesome based on styles because Tyson doesn't fight on the back foot. So whilst Tyson would find some opponents alot easier, maybe 1 or 2 could be more troublesome based on styles.
Well, maybe, if Tyson can miraculously stay at his '88 form all through the period in which Holyfield was an elite force. By miraculous, I mean that would have been a miracle even for a steady focused Tyson.
Tyson blasts out good fighters like Moorer, Cooper and Rahman early. Bowe and Lewis are tough fights to pick but I don't see anyone else causing issues.
Tyson beats them all besides Lewis, Bowe is a 50/50 fight imo. I guess we are assuming that Tyson stays in his 1988 form? Holyfield's tenure as an elite Heavyweight spanned about a decade, so realistically Tyson would be in his 1988 prime when facing the 1990 version of Douglas, and in his 1998 form when facing Ruiz. If Holyfield could have maintained his 1992 form up until 2000, he might have been 2-1 against Bowe & 1-1 against Lewis.
You mean Mike at his best or what he actually was at the time in question? In either way it's hard to see anyone except Bowe and Lewis beating him before 2003. Maybe Foreman would be a difficult stylistic match-up, though. How does Mike react if Foreman manages to push him back, like he did everyone else? Those versions of Bowe and Lewis against Tyson at his best... Very hard to say. I love the match-up with Bowe even more than the one against Lewis, actually. That would just be fireworks for as long as it lasted.
I think Bowe and Lewis would clearly be 2 toughest opponents for best version of Tyson. Old Foreman would be too slow for him, Moorer won't be able to take his power. Mercer would pose some troubles but lose by decision. Not fully focused Douglas won't be able to withstand the best version of Tyson. I think Bowe would be the biggest threat for that version of Tyson, considering his combination of size, skills, power and (probably most important) - workrate and stamina. Lewis' size, skills and ATG clinching ability would also pose a lot of problems for Tyson, who, even at his best, was very vulnerable for clinches (watch James Smith fight, and Smith wasn't as good at tying his opponents in clinches as Lennox was). But I think Lewis' questionable chin would eventually get hit by Tyson and big man would be knocked out.
