Basically Tyson 88 has an extended 12 rounds intensity equal to the intensity of Mike 96 in the first 5 rounds
Tyson by Decision, or late TKO
I'd give a young Tyson the edge. I know Holyfield dominated a post jail Tyson, but a very young Tyson was much quicker, and way better trained. Tyson trained as hard as anyone ever, in 1988.
I think Holyfield would have always beaten Tyson no matter when they fought. Holy just wasn't intimidated by Mike and had a great chin to take his shots. Even if they had fought in 1989-1990 before Tyson lost to Buster Douglas, I thought Holy would have beaten him. Holyfield had better all around skills than Tyson, was also a tough, determined fighter, and was never afraid of Mike. Honestly though, I think the question you're asking is a little unfair because you're asking how would an aging Holyfield done against a prime Tyson. The question is how a prime Holy at HW would have done against a prime Tyson. That's a bit more fair.
No question 88 Mike Tyson beats an advanced 36 year old Evander Holyfield of 96 maybe even stops him.
If they had fought when there were supposed to in late 89-90 Evander would still beat him, Tyson was immediately different after Rooney was fired. Fighting Evander with no real game plan would be devastating. Evander would likely stop him or beat him by a wide margin.
If the 88 Tyson who had Rooney fought the Evander of 1990 now thats a fight it would be hard to pick. Likely a close decision win for one of them.
There was never a time in Holyfield's or Tyson's lives that Evander Holyfield didn't own Mike Tyson. Mike at his best was never equal to Evander at even a diminished capacity. As teenagers during the Olympic trials Mike was punking out people over a pool table and Holyfield (21 to Mike's 17 years of age) put Mike in his place and forever established psychological dominance over Mike. It never changed throughout the rest of their lives Mike was subordinate and Evander dominant. The fact that Evander was a far more skilled boxer just intimidated Mike all the more.
Holyfield is superior to Tyson and will always have Mike's numbers.
I would say a Tyson knock out in 6 rounds. Probably less.
^ This.
It's my statistical analysis
Basically Tyson 88 has an extended 12 rounds intensity equal to the intensity of Mike 96 in the first 5 rounds