BoxRec

Had Holyfield immediately would've taken on Tyson upon moving up to HW.

As the man, who became Undisputed at cruiserweight with a win over DeLeon - under the rules, he most likely would've received an immediate title shot at Mike Tyson, who was Undisputed HW champ.

Fight takes place in summer or early fall of 1988.

Holyfield isn't fighting Tillis. Tyson doesn't split with Rooney after Spinks win.

Who wins between Tyson and Holyfield in 1988?

2128778 wrote: ↑01 Mar 2026, 06:26 Had Holyfield immediately would've taken on Tyson upon moving up to HW.

As the man, who became Undisputed at cruiserweight with a win over DeLeon - under the rules, he most likely would've received an immediate title shot at Mike Tyson, who was Undisputed HW champ.

Fight takes place in summer or early fall of 1988.

Holyfield isn't fighting Tillis. Tyson doesn't split with Rooney after Spinks win.

Who wins between Tyson and Holyfield in 1988?

Holyfield on points. Evander has completely the wrong style for Tyson.

Tyson mid to late round stoppage.

I'd take Holyfield to win a UD over Mike in 1988. He still hadn't fully developed his Heavyweight Body so I don't think he'd have had the power to stop Mike at this point in their careers, but he had the athleticism, and Boxing ability over Mike, and the heart and the stamina over Mike, and the chin and the height and the reach over Mike, and the will and the mental fortitude over Mike.

Holyfield beats Mike Tyson in 1988 for the same reason he beat him in 1996. He's a better fighter.

1988 is the only year that I think Tyson would have a chance to beat Holyfield. As stated above, Holyfield's heavyweight body was not fully developed yet, and Tyson's technique was still very tight. Evander was always the tougher guy, so I see a war. 50-50 bout, imo.

goose 5 wrote: ↑01 Mar 2026, 12:22 1988 is the only year that I think Tyson would have a chance to beat Holyfield. As stated above, Holyfield's heavyweight body was not fully developed yet, and Tyson's technique was still very tight. Evander was always the tougher guy, so I see a war. 50-50 bout, imo.

The same way I see it. The great Evander Holyfield's body wasn't fully developed in 1988 to fight the great Mike Tyson at heavyweight. Still, if Tyson wins, it would have been the toughest win in his career.

And like you said goose5: It would be Iron Mike's best chance to beat Holyfield at that time.

But, if they fight after 1988, Holyfield wins every time and twice on Sunday. He was the better fighter overall.

Mike, probably by Knockout.

gilgamesh wrote: ↑01 Mar 2026, 10:21 I'd take Holyfield to win a UD over Mike in 1988. He still hadn't fully developed his Heavyweight Body so I don't think he'd have had the power to stop Mike at this point in their careers, but he had the athleticism, and Boxing ability over Mike, and the heart and the stamina over Mike, and the chin and the height and the reach over Mike, and the will and the mental fortitude over Mike.

Holyfield beats Mike Tyson in 1988 for the same reason he beat him in 1996. He's a better fighter.

For me, Mike would have to be a substantial favorite in that fight. By a clear margin.

2354595 wrote: ↑14 Mar 2026, 17:52

gilgamesh wrote: ↑01 Mar 2026, 10:21 I'd take Holyfield to win a UD over Mike in 1988. He still hadn't fully developed his Heavyweight Body so I don't think he'd have had the power to stop Mike at this point in their careers, but he had the athleticism, and Boxing ability over Mike, and the heart and the stamina over Mike, and the chin and the height and the reach over Mike, and the will and the mental fortitude over Mike.

Holyfield beats Mike Tyson in 1988 for the same reason he beat him in 1996. He's a better fighter.

For me, Mike would have to be a substantial favorite in that fight. By a clear margin.

Oh, yes!

2354595 wrote: ↑14 Mar 2026, 17:52

gilgamesh wrote: ↑01 Mar 2026, 10:21 I'd take Holyfield to win a UD over Mike in 1988. He still hadn't fully developed his Heavyweight Body so I don't think he'd have had the power to stop Mike at this point in their careers, but he had the athleticism, and Boxing ability over Mike, and the heart and the stamina over Mike, and the chin and the height and the reach over Mike, and the will and the mental fortitude over Mike.

Holyfield beats Mike Tyson in 1988 for the same reason he beat him in 1996. He's a better fighter.

For me, Mike would have to be a substantial favorite in that fight. By a clear margin.

He was a 25 to 1 favorite in 1996 when Holyfield kicked his ass.

gilgamesh wrote: ↑15 Mar 2026, 11:59

2354595 wrote: ↑14 Mar 2026, 17:52

gilgamesh wrote: ↑01 Mar 2026, 10:21 I'd take Holyfield to win a UD over Mike in 1988. He still hadn't fully developed his Heavyweight Body so I don't think he'd have had the power to stop Mike at this point in their careers, but he had the athleticism, and Boxing ability over Mike, and the heart and the stamina over Mike, and the chin and the height and the reach over Mike, and the will and the mental fortitude over Mike.

Holyfield beats Mike Tyson in 1988 for the same reason he beat him in 1996. He's a better fighter.

For me, Mike would have to be a substantial favorite in that fight. By a clear margin.

He was a 25 to 1 favorite in 1996 when Holyfield kicked his ass.

Not even close to the same Mike and Holyfield wasn’t yet where he would be.

As an aside, most books closed at around 6-1 on the first Tyson-Holyfield fight, although it opened much wider.

2354595 wrote: ↑15 Mar 2026, 12:02

gilgamesh wrote: ↑15 Mar 2026, 11:59

2354595 wrote: ↑14 Mar 2026, 17:52

For me, Mike would have to be a substantial favorite in that fight. By a clear margin.

He was a 25 to 1 favorite in 1996 when Holyfield kicked his ass.

Not even close to the same Mike and Holyfield wasn’t yet where he would be.

As an aside, most books closed at around 6-1 on the first Tyson-Holyfield fight, although it opened much wider.

Holyfield wasn't at his best in 1996 either. He was just still better than Mike.

If Mike was "past his best" then he has no excuse. Holyfield was older than him, and had been in more tough fights than him, yet he wasn't as used up as Mike? The only reason why that could be is because he was simply ALWAYS better than him.

gilgamesh wrote: ↑15 Mar 2026, 13:04

2354595 wrote: ↑15 Mar 2026, 12:02

gilgamesh wrote: ↑15 Mar 2026, 11:59

He was a 25 to 1 favorite in 1996 when Holyfield kicked his ass.

Not even close to the same Mike and Holyfield wasn’t yet where he would be.

As an aside, most books closed at around 6-1 on the first Tyson-Holyfield fight, although it opened much wider.

Holyfield wasn't at his best in 1996 either. He was just still better than Mike.

If Mike was "past his best" then he has no excuse. Holyfield was older than him, and had been in more tough fights than him, yet he wasn't as used up as Mike? The only reason why that could be is because he was simply ALWAYS better than him.

I couldn’t disagree more.

Agreed that Holyfield was the better man but the 4 year layoff experienced by Tyson certainly was no help to him.

I agree with Gilgamesh, Holyfield was better anyway and the excuses sound kind of absurd in retrospect.
People were genuinely concerned for Holyfield's life heading into the first match, as he had the heart health issue, and had already had a full career really at cruiser and heavy and was older. How can this all wind up reflecting better on Tyson? Holyfield was more used up than Tyson and he beat him down and then made him essentially quit the second time. People make so many excuses for Tyson, in every regard, it's ridiculous.
I think he would have stopped him in 88, maybe even easier. Why does Tyson get credit for being older against Holy but Holy being younger wouldn't count? I get that he wasn't as big, but Tyson also wasn't as experienced. He might crack even easier.

To me - I think, the proposed time period is that short window, where Tyson could've won that fight. Holyfield wasn't having it easy in his first couple of fights at HW and needed some time to acclimatize to the new division.

2128778 wrote: ↑20 Mar 2026, 03:47 To me - I think, the proposed time period is that short window, where Tyson could've won that fight. Holyfield wasn't having it easy in his first couple of fights at HW and needed some time to acclimatize to the new division.

I agree with you. That's the only time frame that Iron Mike Tyson could ever beaten Evander Holyfield. That's circa (1988-89). Holyfield wasn't accustomed to the heavyweights yet.

But, a prime Holyfield at heavyweight, circa 1990-94 or beyond, always beats Tyson.

Tyson looked very sloppy against Bruno in 1989- Holyfield-who beat Dokes the following month- would have stopped him that night.

goose 5 wrote: ↑20 Mar 2026, 21:12 Tyson looked very sloppy against Bruno in 1989- Holyfield-who beat Dokes the following month- would have stopped him that night.

Yes. But Holyfield was having difficulties with Dokes, too. And that Dokes was past it.

My point is, past 1988 - it's likely Holyfield's fight.

If it happens in mid-to-late 1988, with Holy taking on Mike immediately without no tune-ups and with Mike coming off Spinks destruction - I can see Tyson being favoured.

2128778 wrote: ↑21 Mar 2026, 05:20

goose 5 wrote: ↑20 Mar 2026, 21:12 Tyson looked very sloppy against Bruno in 1989- Holyfield-who beat Dokes the following month- would have stopped him that night.

Yes. But Holyfield was having difficulties with Dokes, too. And that Dokes was past it.

My point is, past 1988 - it's likely Holyfield's fight.

If it happens in mid-to-late 1988, with Holy taking on Mike immediately without no tune-ups and with Mike coming off Spinks destruction - I can see Tyson being favoured.

That would have been suicidal for Evander Holyfield to challenge Mike Tyson without a couple of tune up fights.

The 1988-89 time frame was the better one time for Tyson to beat Holyfield. Anything after 1990, it would be all The Real Deal.