You can only watch one of these Holyfield Fantasy matchups...

Discussion in 'Classic Boxing Forum' started by Rubber Glove Sandwich, Mar 12, 2026.


Which fight do you make happen?

  1. Holyfield vs Usyk (Cruiserweight)

    22.7%
  2. Holyfield vs Frazier

    29.5%
  3. Holyfield vs Tyson (1988)

    43.2%
  4. Holyfield vs Marciano

    2.3%
  5. Holyfield vs Dempsey

    2.3%
  1. Rubber Glove Sandwich

    Rubber Glove Sandwich A lot of people have pools Full Member

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    You're only able to watch one of the following 5 Holyfield fantasy fights. Which one do you go see?
     
  2. Marvelous_Iron

    Marvelous_Iron Active Member Full Member

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    88 Rooney Tyson to settle it once and for all
     
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  3. TNSNO1878

    TNSNO1878 Well-Known Member Full Member

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    I think it has to be the Usyk one because it would be a definitive answer to who is the greatest cruiserweight of all time. I think the Usyk one is the closest to a 50/50 it gets.
     
  4. Melankomas

    Melankomas Corbett beats your favourite fighter

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    Holyfield vs. Frazier
     
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  5. Spreadeagle

    Spreadeagle Active Member Full Member

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    Feb 24, 2023
    Agreed .
     
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  6. Spreadeagle

    Spreadeagle Active Member Full Member

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    Holyfield vs Usyk is now my favourite fantasy-fight.I would pay a huge sum of money
    to be at ringside for that one.It's probably the most difficult fantasy fight in which to pick the winner.
     
  7. slash

    slash Boxing Addict Full Member

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    (Prime) Holyfield be landing nasty body shots. Oh, yes. Holyfield would hit Bowe with a nasty body shot, and Bowe would turn to the ref and motion like he got head-butted. ****ed him all up. Made him a ***** lips.

    Probably Holyfield-Frazier.. no backward steps. Holyfield always beats Tyson. (So keep on talking about Bert Cooper)
     
  8. Spreadeagle

    Spreadeagle Active Member Full Member

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    Mate....I think you are somewhat confused....Bowe ?
     
  9. OddR

    OddR Well-Known Member Full Member

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    Torn between the first 3
     
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  10. AwardedSteak863

    AwardedSteak863 Boxing Addict Full Member

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    Aug 16, 2018
    Holyfield vs Uysk for sure. Does Holyfield's will overcome Uysk's skill? Before someone says it, I'm not saying Holyfield isn't skilled, I want to see what Uysk would do when skill isn't enough. Prime Holyfield had tons of skill but he also was willing to go places in a fight that we haven't seen Uysk have to go yet because he is so ****ing good. I'm not sure that there is a fantasy fight that I would rather see than Holyfield vs Uysk.
     
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  11. SgrRyLeonard

    SgrRyLeonard Active Member Full Member

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    Holyfield vs Tyson '88 would answer a lot of questions.
     
  12. Jel

    Jel Obsessive list maker Full Member

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    Holyfield-Frazier and Holyfield-Marciano are can’t-miss classics but Holyfield-Tyson from ‘91 is the one we really missed out on. I’d favour the Tyson of 1988 against the Holyfield of ‘88 but by 1991, I’d lean towards Evander.
     
  13. Fergy

    Fergy Walking Dead Full Member

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    Tyson 88 , to settle the damn argument once and for all!!
     
  14. Yorbals

    Yorbals Well-Known Member Full Member

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    Frazier
    I think Holyfield would beat Usyk, Frazier would as well
    Usyk is good but he’s massively overrated due to beating men that these two would also have beaten
     
  15. Eddie Ezzard

    Eddie Ezzard Boxing Addict Full Member

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    The Dempsey one would be great. Give us some idea how the old timers cope against a modern great. Whoever wins, it would create a storm of 'Told you so' on here among the advocates of either era.

    My picks. Holy tko Dempsey, too skilled. Busts him up. Ditto Marciano. He's better than the version of Ezzard Charles who ran Rocky close. Big enough and strong enough to keep Marciano off him while his work accumulates damage. Frazier too relentless and strong. Joe's bodywork pays off over 15 for a points decision. 88 Tyson gets to him at some point in 88 and doesn't let him off the hook. Evander gets to Usyk's body eventually and wears him down to get a points or stoppage.