The Holmes that was knocked out by Tyson vs the Holmes that lost to Holyfield

It still leads to a Tyson KO for mine. Holmes wasn't going to survive him.

 

He could have won if he fought Tyson like Evander did: Tie him up, Jab the hell out of him, muscle him around and foul him egregiously. Of course, old Larry would have to execute this perfectly, but it is feasible.

 

I doubt that the 92 version does any better . It would have been interesting to see if the 88_92 Holmes beats the Tyson who holyfield beat. I've long thought he would have.

 

Holmes got knocked out as soon as he actually tried winning. He was just trying to survive for the first 2.5 rounds.
That's how it would have been with any version of Holmes. Tysons body hooks under the jab and overhand right over the jab were a stylistic nightmare for Holmes and fighting off the ropes like an older Holmes liked to do is also a terrible idea against Tyson. He could brace himself against Holmes and Mercer onslaught while resting his legs against the ropes but against Tyson he wouldn't see the punches coming and if you don't make Tyson reset by pushing him back and beating him up then he just builds too much momentum

 

That Tyson was predicable and Holyfield had figured him out. Holyfield watched all of Tyson's fights and studied him. He knew what he had to do after Rooney was gone.

Holmes was fighting a prime, peak Tyson with Rooney in his corner. He wasn't going to win that night. Holmes at his best wouldn't have beaten that Tyson. Even that strategy wouldn't work

 

Bingo.

 

Er, Holyfield beat him quite comfortably.

 

Against a prime 21 year old Tyson of 1988, there's nothing a 1985-onwards Holmes could have done that would result in a win, he was just too old. The 1992 version wouldn't last the distance either.
Whether a hypothetical 1988 version with some tune-ups would have lasted the distance, I don't know. I wouldn't rule it out but I'd probably expect a stoppage win for Tyson anyway, sooner or later, despite a better showing from Holmes.
A 38+ year old Holmes cannot beat the best ever version of Tyson, age 21.

Prime Holmes though, that's a different matter.
The Larry Holmes of 1978 would have taken Tyson apart.

 

Both versions of Larry Holmes were well past their primes, neither were even close to the peak years of 1978-1982. He began to decline in 1983 before his title defense against Tim Witherspoon. The Holmes that was kayoed by Mike Tyson on Jan 22 1988 had been retired since the second Michael Spinks fight in 1986. The Larry Holmes that fought Evander Holyfield and Ray Mercer in 1992 was very well past his prime too.