The greatest fantasy boxing matches that could have happened

Discussion in 'Classic Boxing Forum' started by Jel, Jun 27, 2025.


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  1. Jel

    Jel Obsessive list maker Full Member

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    This thread is for fights that looked like they were either going to happen or fights that could feasibly have happened but never did (so no ‘Sugar Ray Robinson v Sugar Ray Leonard’ mentions… unless you really wanted to see a septuagenarian Robinson get assaulted).

    If you like, you can also say what year it would have ideally taken place in, why you think the fight didn’t happen, who would have won had it happened and what the impact of it would have been on boxing history.
     
    Last edited: Jun 27, 2025
    Jel, Jun 27, 2025
    Jel, Jun 27, 2025
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  2. Jel

    Jel Obsessive list maker Full Member

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    I’ll start:

    Riddick Bowe v Lennox Lewis, undisputed heavyweight championship, 1993


    Why didn’t it happen?
    In 1992, Bowe dumped his WBC title in the bin rather than face Lewis, his no. 1 contender. Lewis won the vacant title so there was still a chance for a unification fight in 1993, but Bowe chose to rematch against Holyfield and lost the title.

    Who would have won?
    Many people point to Lewis beating Bowe in the Olympic final in 1988 as a barometer to what would have happened in the pros. Others point to Lewis’s later heavyweight career as an indicator that he was better than Bowe, plus Bowe’s indiscipline post-title win. But both fighters were flawed at this point in their careers - Lewis was leaky defensively and more aggressive at that point, making him open to Bowe counters. Bowe was also an excellent body puncher. Conditioning would have played a part too. My pick is Bowe by mid-rounds KO in a fight where both men have their moments.

    What impact would it have had?
    A Lewis defeat would have meant back to the drawing board, which wasn’t much different from what happened following his KO loss to Oliver McCall. A Bowe defeat may have simply hastened the decline we witnessed from him.
     
    Jel, Jun 27, 2025
    Jel, Jun 27, 2025
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  3. Greg Price99

    Greg Price99 Boxing Addict Full Member

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    Mickey Walker was either scheduled, or deep in talks (I read a biography on Leonard a couple of years ago and forget which), to defend his WW crown against Benny Leonard around 1924.

    Why didn't happen - Iirc Leonard suffered a hand injury.

    Who would have won - I think Leonard was marginally better p4p and Walker's greatness is based on his exploits above, rather than at, WW, however, Walker's size advantage makes him a very narrow favourite for either a late stoppage or close points win, for me.

    What impact would it have had - If Walker won, I doubt either would be appraised differently. Leonard ended his LW career an incredible 81-0, which included some wonderful opposition. If he'd have added the WW title against a prime ATG, he'd probably make mine, and possibly some others, top 5 p4p ATGs.
     
    Greg Price99, Jun 27, 2025
    Greg Price99, Jun 27, 2025
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  4. greynotsoold

    greynotsoold Boxing Addict

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    Ray Robinson v Charley Burley.
     
    greynotsoold, Jun 27, 2025
    greynotsoold, Jun 27, 2025
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  5. Barrf

    Barrf Boxing Addict Full Member

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    how about Charley Burley against any title holder? talk about a superb boxer who completely got the short end of the stick. never got to make any real money, worked regular jobs in addition to boxing. if Burley were around and his prime today, he'd be retired a rich man by age 35.
     
    Barrf, Jun 27, 2025
    Barrf, Jun 27, 2025
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  6. Stevie G

    Stevie G Obsessed with Boxing Full Member

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    Lennox loses in 1993 but gets revenge after hooking up with Emmanuel Steward.
     
    Stevie G, Jun 27, 2025
    Stevie G, Jun 27, 2025
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  7. Stevie G

    Stevie G Obsessed with Boxing Full Member

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    Floyd Mayweather v Manny Pacquaio in 2009
     
    Stevie G, Jun 27, 2025
    Stevie G, Jun 27, 2025
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  8. Journeyman92

    Journeyman92 Prayers for Pacman Full Member

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    It’s a fight I’ve felt Robinson would’ve won - how about you?
     
    Journeyman92, Jun 27, 2025
    Journeyman92, Jun 27, 2025
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  9. Stevie G

    Stevie G Obsessed with Boxing Full Member

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    I also feel that Robinson would have won but Burley would have given him a great fight.
     
    Stevie G, Jun 27, 2025
    Stevie G, Jun 27, 2025
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  10. Jel

    Jel Obsessive list maker Full Member

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    Well, yeah, or at 2009/2010 for sure… but I wasn’t thinking about fights that ultimately took place: e.g. Holyfield v Tyson in 1991 when they ultimately met in 1996.
     
    Jel, Jun 27, 2025
    Jel, Jun 27, 2025
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  11. Journeyman92

    Journeyman92 Prayers for Pacman Full Member

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    Kostya Tszyu vs De La Hoya / Mayweather both were at one time possible. Mayweather still wins but it’d have at least been a great bout.
     
    Journeyman92, Jun 27, 2025
    Journeyman92, Jun 27, 2025
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  12. Stevie G

    Stevie G Obsessed with Boxing Full Member

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    Sugar Ray Leonard - Thomas Hearns III in November '89. Would have been a great fight instead of the lacklustre one between Ray and Roberto that happened in reality.

    Chris Eubank-Nigel Benn III in early 1994.
     
    Stevie G, Jun 27, 2025
    Stevie G, Jun 27, 2025
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  13. Stevie G

    Stevie G Obsessed with Boxing Full Member

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    Roberto Duran-Alexis Arguello.
     
    Stevie G, Jun 27, 2025
    Stevie G, Jun 27, 2025
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  14. drenlou

    drenlou VIP Member Full Member

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    I think Hamed-Marquez would have been a hell of a fight. Also Chavez-Trinidad in the mid 90s almost happened as well.
     
    drenlou, Jun 27, 2025
    drenlou, Jun 27, 2025
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  15. Stevie G

    Stevie G Obsessed with Boxing Full Member

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    Joe Frazier-Ken Norton. Yes I know that they were friends but Frazier once said in an interview that if someone had come up with the right financial incentive they'd have fought.
     
    Stevie G, Jun 27, 2025
    Stevie G, Jun 27, 2025
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