Sorry if this one's been done before, but would the outcome have been different if they'd fought on Nov 8th 1991? My pick is the same as it was back then, Tyson by 8th round TKO.
They were both better fighters in 1991. I think Holyfield still would have beaten him, but it may have been a closer fight.
I think Holyfield would have ground out the decision in 1991. Even in an interview when asked about the revitalization of his career Tyson said, "My career? My career was over in 1990." He'd already lost the love of boxing by then and it was evident even from his remarks about the Bruno fight onwards. He wasn't taking boxing seriously anymore and had too much else going on in his life. In 1989, Tyson wins by stoppage. The animal that ran through Spinks, Berbick, Tubbs, Biggs and a faded Larry Holmes was one of the most brutally effective fighting machines to ever step into the squared circle.
Holyfield by stoppage. The fight would pan out pretty much as their first fight did, slightly closer however. A lot of Tyson's opponents were beaten the second the contracts were signed - barring Buster Douglas, Evander was the only man to stand up to Tyson during the period when Tyson was anything like prime - both were faded by 1996.
Holyfield still wins a decision or stops Tyson late. Both were better fighters than they were in 96 but Mike had just started the downslide while Evander was at his peak.
Yes, they were both better fighters, but I'm not so sure Holyfield was as wise a fighter back in 1991 as he would become a few years later? Back in 1991, Holyfield was more likely to trade with Tyson instead of trying to counter! Don't forget, Tyson was very sharp, even in 1991. Post Douglas he beat Tillman, Stewart, & Ruddock twice! I don't care what anybody says, but no one expected Tyson to deal with Stewart the way he did! Alex gave Holyfiedl one hell of a fight some fifteen months earlier! Tyson's win over Stewart is often overlooked because of how quickly it was over! The Ruddock fights showed Tyson was a sharp fighter. Ok, so he did not get rid of him in quick fashion, but he did pound upon him, gave him a beating! Tyson's body attack in fight one was particularly impressive, something commentator Lennox Lewis eluded to! In the rematch, Ruddock suffered a broken jaw! Holyfield would have been drawn in fight Tyson's type of fight. I'd say Tyson by late TKO or UD!
Holyfield has never feared Tyson and was an offensive machine in 1991.Holyfield was always confident he could beat Tyson and he proved he was right.
Tyson might have underestamated Holyfield in 1991. He could have seen him as a blown up Cruiser and maybe thought he would disposse of him like of Spinks. That could be his downfall right there. But no way does Holyfield stop the 1991 Tyson. Tyson was in shape, sharp and somewhat hungry and ready for a brawl (as the Ruddock fights show). Evander could probably win a descision if he fought a very smart fight. If Tyson did take Holy seriously who knows what could have happened? But I seem to remember Tyson getting very confident and being too proud of his chin after taking quite a few of Ruddock's bombs (he even started mocking Foreman after this point, mentioning him as an old man he would destroy or something like that). He did say he had no respect for Spinks or his power and he wanted to take him out in 1 so who says he wouldnt think the same of Holyfield? That could be a loss for Mike right there. He did think of Holyfield as an old washed up guy in 1996 and he was super confident he would walk through him as he himself said. Underestamating an opponent is as serious as being out of shape. Tyson of 86-88 however either stops Holyfield or wins a descision.
I see it like this, Tyson spends 3 years inactive, then has 4 nothing fights that wouldn't even count as good sparring sessions, & it still took Holyfield 11 rounds to win, & up to the 6th round it was fairly even. 1986-88 Tyson gives Holyfield a beating, 1991 its a bit closer but still a win for Tyson.