The fight in 96' was a pretty tough fight for both guys. It was not an easy win for Holy. Although Holy had declined by 96' it was not to the extent that Tyson had. If Mike were an average puncher he would have been fodder for anyone after 95', his skills were were seriously diminished. In 91', this is a 50/50 fight. Tyson might even have the edge.
Holy had a hell of a time against Tyson. That was after Tyson was off 3+ years while Holy was fighting high level comp. In 91' Holy had not filled out fully yet also. He very well may have gotten stopped.
I wouldn't say Holy had a hell of a time against Tyson. Tyson got shot good shots in that's for sure, but Holy was able to absorb them and out punch and and out box him, they may well have shared the early rounds but from round 6 onwards it was almost all Holyfield. Holyfield let's not forget had only just got medical clearance to fight back in 96, so it was fully expected that the 96 version of Tyson would easily KO Holyfield. Even if Holyfield was not fully filled out in 91, he would still have more speed to counter that. The key to beating Tyson was putting someone who had a great chin, greast boxing skills and fast hands and someone that enjoys the battle. Holyfield had all of these qualities.......and Tyson hated this type of opponent. So even a lighter Holyfield still gets my vote over a 91 Tyson.
That was to be and it didn't come b'cause Tyson got injured in training and later in a Indiana Court of Law March 1992. Holyfield took on substitutes Bert Copper who rocked him and knocked him down in the Omni in Atlanta and Larry Holmes who sliced Holyfield's eyebrow and had his moments up towards the end stretch with his jab. I believe that taking this in consideration and Tyson's fights with Ruddock, Mike would have taken it... And I am a big Holyfield fan.
My point is that if Holyfield was very hungry like he was in Nov 1990 against Douglas and against Foreman in April 1991, Mike would eat a lot of leather and then you can never know... Cause Mike went down in January 1990 much before Desiree Washington and you can't just say Mike was feelin bad in Tokyo or that that was a fluke. However, Holyfield made a lot out of his trilogy with Bowe and Tyson didn't get the rust off with either Bruno or whoever else he knocked out in 1, get it?
Evander beats this Tyson in dominating fashion. He's just a better fighter than Iron Mike. This would be a couple of notches worse than the beating a supposedly washed up Holyfield actually put on Mike a few years later.
Given that Tyson struggled against James Tillis and had hard battles with Rudduck, who subsequently got KOed by Lewis in 2 ,and Morrison in 5......I'd say Holyfield takes it! Also you have to remember that Bert Cooper was a late late substitute for Francesco Damiani who was a totally different boxer to Cooper, for a start Copper was only 5' 11' ......Damiani was 6' 3" . Holyfield would have specifically trained for Damiani, not Cooper. Also Holyfield had Cooper down with a wicked body shot in the first round ,and was winning the fight easily, and I think complacency set in a little before he got tagged by Cooper. One thing's for sure Holyfield would have been fully prepared against Tyson, and would NEVER get complacent against Tyson in the ring. So I think the Cooper fight has to be taken in that context really.