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Dream Bouts: Floyd Mayweather, Jr. vs. Boxing's All-Time Greats

Updated on January 20, 2016

Legends of The Game

Floyd Mayweather, Jr. Knocked out the undefeated Ricky Hatton in the tenth round.
Floyd Mayweather, Jr. Knocked out the undefeated Ricky Hatton in the tenth round. | Source
An aging Pernell Whitaker loses a close, controversial decision to Oscar De La Hoya.
An aging Pernell Whitaker loses a close, controversial decision to Oscar De La Hoya. | Source
J.C. Chavez  knocked out undefeated Jr. Welterweight champion Meldrick Taylor in 12 rounds.
J.C. Chavez knocked out undefeated Jr. Welterweight champion Meldrick Taylor in 12 rounds. | Source
Manny Pacquiao lands a right hook on Miguel Cotto on his way to scoring a 12th round knockout.
Manny Pacquiao lands a right hook on Miguel Cotto on his way to scoring a 12th round knockout. | Source

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Money Mayweather vs. The Best of Other Eras

Floyd Mayweather, Jr. has won titles in five weight divisions which are: Jr. Lightweight, Lightweight, Jr. Welterweight, Welterweight and Jr. Middleweight. He is one of the best defensive fighters in history and he is the top boxer of his era. He has fought and beat some of the best of his time and he currently has an undefeated record of 44 wins and no losses. The following dream fights are assuming they take place in the Welterweight division. (147 Pound Weight Class)


1. Floyd Mayweather vs. Sugar Ray Robinson: One of the best defensive boxers ever pitted against one of the best offensive fighters ever. Mayweather lands his lead right or a few rounds until Robinson begins to counter it. A close fight throughout with Robinson edging the late rounds by landing his jab, possibly scoring a knockdown and finally cracking Mayweather's defense to earn a close but unanimous decision victory. Robinson W12 Mayweather.

2. Floyd Mayweather vs. Sugar Ray Leonard: This would be a dream fight for sure. The rounds would be very close with Leonard having problems with Floyd's defense and Sugar Ray giving Mayweather fits with his speed and accuracy.The bout would be great for purist because these pugilists have great footwork. Leonard would pull ahead slightly with his activity to take a close decision. Leonard W12 Mayweather. Note: This match could end up being Mayweather W12 Leonard also.

3. Floyd Mayweather vs. Felix Trinidad: Trinidad was a deadly welterweight puncher so danger would always loom during this contest. Tito would win 2 or 3 of the early rounds but after Mayweather figures him out and gets the timing down it would be just a formality. Mayweather pot shots Trinidad down the stretch with lead left hooks and lead right hands to take a competitive but clear unanimous decision over the Peurto Rican legend. Mayweather W12 Trinidad.

4. Floyd Mayweather vs. Henry Armstrong: Floyd would be able to counter the windmill known as Henry Armstrong and slip punches enough to win rounds but Armstrong never stopped punching. Mayweather would keep it close with his textbook shots but Armstrong would win on sheer punch volume and eventually Mayweather would become completely defensive because Armstrong s a devastating puncher to say the least. Armstrong W12 Mayweather.

5. Floyd Mayweather vs. Kid Gavilan: The Kid would be competitive and all the rounds would be close but in the end Gavilan did not have enough power to keep Floyd honest. As the rounds mount Mayweather would start to out class and out land the Cuban. The final few rounds would be dominated by Floyd making his opponent miss and making him pay. Mayweather W12 Gavilan.

6. Floyd Mayweather vs. Manny Pacquiao: The Super Fight that never happened would have been a great fight for the fans. The punch volume of Pacquaio would certainly win him a few stanzas but the defense and overall ring generalship of Money Mayweather would tell in the last 5 or 6 rounds. Mayweather might get wobbled once or twice but then he will jab, slip, hold and land lead rights on the left handed Filipino to earn a unanimous decision victory. Mayweather W12 Pacquiao.

7. Floyd Mayweather vs. Pernell Whitaker: Sweet Pea vs. Pretty Boy. Two of the premiere defensive boxers of all time. This would be a tactical match without many punches landing on either man. Mayweather will and some lead rights but otherwise he would be shut down offensively. Whitaker would land solid right sticks but he too would not mount an offensive. Styles make fights and these two would be landing single jabs and not much else. Mayweather Draw in 12 Whitaker.

8. Floyd Mayweather vs. Thomas Hearns: Even though Mayweather was better defensively Hearns is one of the hardest punchers pound for pound in prizefighting. Mayweather would try to pot shot and clinch which would work for a short time. Hearns would take several rounds trying to catch Floyd while eating occasional right hands from Floyd. Mayweather is far to skilled to get knocked out but Hearns was taller, had a longer reach and he had a masterful jab. After 12 rounds of boxing Hearns wins a decision. Hearns W12 Mayweather.

9. Floyd Mayweather vs. Emile Griffith: These two boxers fought very similar in some ways. It would be nip and tuck with much posturing and feinting. Griffith would win the inside fighting while Money would take control in the center of the ring. The ebb and flow of the bout would keep changing but Mayweather has fast enough hands and a great defense which would allow him to pull it out. Mayweather Wins Majority decision over Griffith.

10. Floyd Mayweather vs. Rocky Graziano: Graziano was a knockout puncher but he had crude ring skills which unless he caught Floyd clean would mean he would be in serious trouble. Mayweather boxes cautious and loses round one but then dominates the rest of the bout. By the 9th round he is landing hooks and uppercuts to go with the jabs and lead rights to open cuts all over Rocky. After the 10th round, a round in which Graziano was wobbled and his face was turned to a crimson mask, his corner calls a halt. Mayweather T.K.O. 10 Graziano.

Floyd Mayweather's overall record for these dream matches is: 5-4-1.Since Floyd is still an active boxer he may accomplish significantly more before he retires which would make me rethink these fantasy bouts.


Pernell Whitaker Highlights

Sugar Ray Leonard Highlights

Birthplace of Floyd Mayweather,Jr.

Sugar Ray Robinson's Greatest Hits

Floyd Money Mayweather's Highlights

© 2013 Buster Johnson

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    • gconeyhiden profile image

      gconeyhiden 2 years ago from Brooklyn, N.Y.C. U.S.A

      Mayweather is a "PROTECTED" fighter in more ways then one. if forced to fight equally talented fighters in neutral arena w.o the benefit of controlling the entire promotion his record wouldn't be what it is plain and simple. i think it fitting that apparently his last KO will be the result of a sucker punch combo. i also find it very amusing and exceedingly dishonest that announcers working his showtime promotions talk of the Ortiz KO as if it resulted from superior boxing and not a kiss and hug of an entirely defensless fighter looking to apologize. i could not help but notice that kenny baylef was exceptionally protective of Mayweather and hence allowed almost no infighting even tho Mayweather was forced to hold Maidana and deserved to be warned. in the entire 2nd bout i heard" punch out" only once. what i did hear over and over from the ref was stop. i cannot recall watching a ref so involvd in a fight. during some of the best action along the ropes he was on the verge of stepping in to give Mayweather breathing room. Im pretty sure Joe Frazier would have smoked his ass if he tried that on him. nowadays i think it almost impossible to get a truly neutral ref in a Mayweather fight that will allow proper infighting. that said the only real fights that involve Mayweather down the road will probably come from speedy fighters who can box Mayweather from outside. this is one reason why id like to see Khan given his chance. if khan is beaten at least it will be on the up and up. forget about Mayweather against the greatest of all time. they didn't need any help in the ring. in mayweather Maidana 2 it seemed at times Mayweather had 3 arms, the 3rd arm being the refs.

    • gconeyhiden profile image

      gconeyhiden 3 years ago from Brooklyn, N.Y.C. U.S.A

      Hi again, OK I have to admit your analysis is pretty good. I didn't like Ali when he first came along but I was always blown away by his ability. Once he backed up his claims in great fights with great fighters it didn't bother me because he had at least in my eyes proven his point. I just don't like it when Floyd says, Ali, Sugars ect. w all due respect I,m the best of all time. Hey, I know it's all hype, as Floyd himself admits, it's his "character" talking, the one trying to figure out how he can make more money then anyone.

    • lesliebyars profile image
      Author

      Buster Johnson 3 years ago from Alabama

      Mayweather is a great defensive fighter right behind the great Willie Pep and Sweet Pea Whitaker but I have an all time top 25 P4P and he barely misses the cut. I don't put him in the top 25 all time or anything and on a non boxing level he is an arrogant guy I don't like. My favorite boxer ever is Evander Holyfield by the way.

    • gconeyhiden profile image

      gconeyhiden 3 years ago from Brooklyn, N.Y.C. U.S.A

      With all due respect Mayweather is not so much about proving he IS indeed as he says THE BEST EVER but more about getting you to believe he IS THE BEST EVER and on that account he has been very successful without actually going out and proving it against the greatest competition out there, Im talking great primed fighters at the top of their game who are in the same class and not too small. Great fighters say...I will fight ANYONE to prove how good I am. Mayweather on the other hand says hey Im already the best and this highly rated game fighter doesn't really deserve a shot at me. Hey Floyd I got news for you, the truly great fighters don't pull that crap. You go after the tough guys gunning for you no matter who they are. You cut the best deal you can then you get in the ring and give the fight fans what they want..great fights, truly memorable fights. Mayweather will never be as great as Ali or the Sugar Rays why? Because these greats knew it was about boxing truly competitive competition and less about maintaining a seemingly perfect record. The truly great fighters Ali, Sugar Rays ect. prove more in their highly contested losses then lesser undefeated fighters can with all their wins. I have to watch more of Floyd's early fights to be honest but I have seen enough in the last 9 years or so to know his weakness. He can be beaten inside if you can get there and stay there. Floyd apparently isn't a great inside fighter as was Ali,the Sugar Rays ect. His shoulder rolls don't work as well in the trenches up close and personal. The posture doesn't allow him to counter effectively so he can be overwhelmed by very aggressive, speedy strong fighters. great fighters like Ray Robinson or Leonard would have distinct advantage once inside. On the outside he would hold no great advantage over them, simply put he would have to fight for his life. Floyd is very talented but almost none if not all of the guys he has beaten would be able to win against the truly great ones. Mosely was past his prime, De La Hoya at 35 just could'nt maintain his pace and his lead in the fight, something he had problems with even when younger. Alvarez was exposed by Trout and I knew he could not win if he didn't press more. Mayweather's no fool and knows Pacqiao is real wild card, hence NO FIGHT. Mayweather has the ability to beat him but still NO FIGHT. I'm sure Sugar Rays, Ali, Duran ect. would fight Pacman but THE VERY BEST EVER...NO!!! Floyd is managing a circus alright.

    • lesliebyars profile image
      Author

      Buster Johnson 3 years ago from Alabama

      I agree with everything you said but if he did fight all the ones I mentioned above he could have beat a few. I'm not a Mayweather lover I love all boxing but his defense and speed is good. Besides I did say he would lose to several of these great boxers if he fought them.

    • gconeyhiden profile image

      gconeyhiden 3 years ago from Brooklyn, N.Y.C. U.S.A

      Mayweather has to get in the ring first against truly great fighters he cannot dominate. History shows he isn't so keen on this idea. Why are most of his opponents long shots...because they are so great or because it's perceived he has an advantage over his opponents. Plain fact is his main advantage over most opponents is his speed but that advantage just would not exist against most of the great ones. He very well could beat pacman but he wont even get in the same ring with him. GREAT. why is that? Don't tell me 40-50 million isn't enough. Pacquiao has speed, aggression, experience and is a southpaw and is considered a great fighter. His head would have looked great on Floyd's mantleplace but Floyd I never lost bling bling won't do what all the other greats would..get in the ring with him. Truly great fighters are scared of nothing.

    • lesliebyars profile image
      Author

      Buster Johnson 3 years ago from Alabama

      His defense would win him many of three bouts. Wet dreams? I'm objective cause I love the sport. Mayweather is not one of my favorites but defense wins fights in many cases.

    • gconeyhiden profile image

      gconeyhiden 3 years ago from Brooklyn, N.Y.C. U.S.A

      you obviously have wet dreams about Mayweather and bought into all the hype. truth is these guys your talking about craved knocking off their rivals and GREAT rivals they were. Mayweather on the other hand is so defensive minded he is smart enough not to go looking for these kinds of fights. He could have had truly great fights the kind that might have proved his claim but its clear he has been avoiding such wars and cares more about his record, his bling, his hype. He truly is a defensive wizard. Wink wink.

    • lesliebyars profile image
      Author

      Buster Johnson 3 years ago from Alabama

      I'm a big Mayweather fan let me say and he is a Great fighter without a doubt but so is Sugar Ray Robinson and Sugar Ray Leonard not to mention the freakish Hitman Hearns.

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      Melvyn 3 years ago

      Sugar Ray Robinson & Thomas Hearns were too tall & powerful for the 5'7 Mayweather. Floyd gets beat up pretty badly

    • lesliebyars profile image
      Author

      Buster Johnson 3 years ago from Alabama

      Mayweather is my favorite fighter but I'm a historian of boxing and I'm just being real.

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      Me 3 years ago

      FLOYD WOULDN'T HAVE LOSS TOO NONE OF THOSE GUYS R U KIDDING ME..........THE CLOSEST WOULD B RAY ROBINSON......KNOWBODY BEATS MAYWEATHER PERIOD.