Interesting question.
Tyson had 2 wars in -91 against “Razor” Ruddock.
He won both but was in heavy decline.
His head movement was more or less gone, he didn’t throw “punches in punches”. Instead he mostly was a one punch head hunter. But proved he could take a punch and that he actually was a pretty good brawler against Ruddock.
Holyfield fought Foreman and Cooper in -91 and honestly he didn't look particular good against either of them with his brawling and going to war tactics.
Holyfield at this time hadn't fully “matured” into a real heavyweight weight yet, while Tyson was a real heavyweight.
Holyfield of -96 and -97 who defeated Tyson was something completely else in size, strength and punching power compared to the the -91 version.
The problem with Holyfield was that he was somewhat inconsistent, he had a extremely high highest level, but also a quite low lowest level as a heavyweight.
And you never really know which version of Holyfield that would show up. The crowd pleasing brawling going to war Holyfield, or the patient technical boxer that he was on a few occasions.
No doubt that Holyfield would have been highly motivated, determined to win and fully trained, but for this particular fight i think that Tyson would have been pretty motivated too. Maybe the most motivated since the Spinks fight in -88 because he had the chance to regain the title.
The outcome of the fight in -91 would depend on which tactics Holyfield would use.
If this version of Holyfield chooses to brawl and go to war against Tyson i don't think he is big or strong enough to bully Tyson around like he did in their actual fights, and then i would favour Tyson on a mid round stoppage.
But if Holyfield fought like he did against “Buster” Douglas the previous year, being patient, using lateral movement, jabbing and countering Tyson i would favour Holyfield on a clear unanimous decision.
