Boxing is one of those sports where, when the hype is real, the fight should just happen—no delays, no politics, just pure action. Fans don’t want to wait years, watching negotiations fall apart and fighters age out of their prime. Right now, we’re hyping up dream matchups like Terence Crawford vs. Canelo Alvarez, Shakur Stevenson vs. Gervonta Davis, and David Benavidez vs. Dmitry Bivol. Everyone’s asking the same question: Who really has the bigger power?

Luckily, we are getting at least one of these mega fights. Canelo Alvarez has signed a four-fight deal with His Excellency Turki Alalshikh, making a September showdown with Terence Crawford a reality. But what about the others? Will we ever see them, or will they go down in history as missed opportunities—just like so many before them? Because let’s be real: Boxing has a long history of dream fights that never happened. So, what are the biggest fights that never materialized? Let’s dive in.

1. Floyd Mayweather Jr. vs. Manny Pacquiao– The Fight That Came Too Late

How It Almost Happened?

For years, fans were dying to see Floyd Mayweather Jr. and Manny Pacquiao go head-to-head. It was the fight that promised to define an era—two of the greatest boxers facing off for ultimate glory. Negotiations started as early as 2009, with talks of a 50-50 purse split for a March 2010 fight. Everything seemed set, and it looked like we were finally going to witness the showdown of a lifetime.

The real breakthrough, though, came from an unexpected source. A Hollywood waiter and part-time actor named Gabriel Salvador. He introduced Pacquiao’s trainer, Freddie Roach, to CBS President Les Moonves, who then worked behind the scenes to bridge the gap between Bob Arum (Pacquiao’s promoter) and Mayweather’s team. With all major roadblocks—purse split, drug testing, and location—sorted out, Mayweather himself publicly challenged Pacquiao in December 2014. The fight was officially set for May 2, 2015, and when it finally happened, it became the highest-grossing fight in history, generating over $600 million.

Why Did It Happen (At the Right Time)?

So, why did it take six years to actually happen? Simple—endless disagreements. The first attempt in 2009 fell apart because of drug testing issues. Mayweather wanted Olympic-style testing, which included random blood and urine tests, but Pacquiao wasn’t comfortable with the unlimited nature of it. Negotiations collapsed. By 2012, Pacquiao had agreed to drug testing, but another issue popped up—money. Money Mayweather offered Pac Man a flat $40 million but refused to split the pay-per-view revenue, which could have earned Pacquiao much more. Unsurprisingly, Pacquiao declined, and the fight was off again.

Mayweather also stirred controversy with racist remarks about Pacquiao, referring to him as “a yellow chump” and making offensive comments about his ethnicity. His remarks sparked widespread backlash, leading him to issue a public apology the following day. “I want to apologize to everybody… I don’t have a racist bone in my body,” Mayweather stated. And then there was the issue of promoters. Mayweather despised Bob Arum (his former promoter), and that alone was a major roadblock.

In the end, when they finally fought in 2015, the hype was insane, but the actual fight? A letdown. Mayweather played it safe at 33, with his signature defense, and Pacquiao, 32, who later revealed he had a shoulder injury, struggled to land significant punches. Some fans even rebranded it as “Better Never Than Late” instead of the “Fight of the Century”. Ironically, Gabriel Salvador, the waiter who made the fight happen, never got paid for his role. Just another twist in the long, complicated story of Mayweather vs. Pacquiao.

2. Riddick Bowe vs. Lennox Lewis – The Heavyweight War That Never Was

How It Almost Happened?

Let’s set the record straight. Riddick Bowe vs. Lennox Lewis was supposed to happen. In fact, it was practically written in the stars after their 1988 Olympic showdown, where Lewis stopped Bowe to win gold. Fast-forward to 1992, and both were top-tier heavyweights. The boxing world wanted a Bowe-Lewis fight, and so did the fighters themselves.

The setup was there. A mini-tournament featuring Bowe, Holyfield, Razor Ruddock, and Lewis. The winners—Bowe (who beat Holyfield in November 1992) and Lewis (who demolished Ruddock in October 1992)—were supposed to face off in 1993. HBO was ready to throw $32 million into the pot.

Then, in 1994, after years of failed negotiations, Big Daddy and The Lion finally signed a deal to fight in March 1995. Everything was on track—until Lewis lost his title to Oliver McCall in September 1994, killing the deal. So, the idea that Bowe was terrified of Lewis? That’s just fanboy nonsense. If he were scared, he wouldn’t have signed the contract in ‘94.

Why Did It Not Happen?

One name: Rock Newman. Bowe’s manager played a massive role in sabotaging the fight in ‘92. Newman didn’t like Lewis or his team and wasn’t about to risk Bowe losing his champion status so soon. Even though Bowe and his legendary trainer, Eddie Futch, wanted the fight, Newman had other plans.

Negotiations turned into a circus. Newman lowballed Lewis with an insulting $3 million offer (out of a $32 million purse). When that didn’t work, he tried getting Lewis to fight on Bowe’s undercard for just $2 million, promising him a title shot later. Lewis’ manager, Frank Maloney, wasn’t falling for it.

Then came the infamous trash-can moment in December 1992. Bowe, convinced that he was being lowballed, publicly dumped the WBC belt instead of fighting Lewis. It was a PR stunt, but after the cameras left, his team fished the belt out of the garbage. By the time Bowe finally overruled Newman in ‘94 and signed the fight, Lewis’ loss to McCall ended the dream matchup for good. Without a world title on the line, promoters wouldn’t pay up, and boxing lost one of its biggest potential fights. Both Bowe and Lewis wanted it. Bad management and bad timing stopped it.

3. Mike Tyson vs. George Foreman – The Battle of KO Kings

How It Almost Happened?

Imagine this: Mike Tyson vs. George Foreman, two of the most fearsome punchers in boxing history, standing toe-to-toe in the ring. It would have been a dream fight, a battle of raw power, aggression, and legendary knockout artists. And at one point, it nearly became a reality. Foreman had been out of the game for a decade before making a shocking comeback in 1987. At 38, he wasn’t just looking for a payday—he wanted Iron Mike Tyson. After racking up 20 straight wins in his comeback, Big George was right in the mix for a big fight.

In 1990, Tyson was coming off his shocking loss to Buster Douglas, and his promoter, Don King, saw an opportunity. He put Tyson and Foreman on the same fight card in April—Tyson knocked out Henry Tillman in 1st round, and Foreman destroyed Adilson Rodrigues in 2nd round. The stage was set. The hype was real. ESPN covered the potential matchup extensively. Everything seemed to be pointing toward a massive showdown between the two knockout kings. But then… it just never happened.

Why Did It Not Happen?

Well, according to Don King’s former matchmaker, Bobby Goodman, the answer is simple: Tyson wanted no part of Foreman. Tyson was known for his ferocity, but when Don King tried to sell him on fighting Foreman, things took a turn. Supposedly, Tyson flipped out, yelling, “I’m not fighting that fu–ing animal! If you love the mothefu–er so much, you fight him!” That’s a pretty extreme reaction.

And honestly, it’s not hard to see why Tyson might have been hesitant. Foreman wasn’t just some washed-up veteran—he was still a terrifying puncher with a granite chin. Tyson thrived on overwhelming his opponents early, but Foreman was the type of guy who could eat those shots and keep coming forward. It would’ve been a nightmare matchup for Iron Mike. Of course, we’ll never know for sure how serious the 50-7, 44 KO boxer’s fear was, but what we do know is that the fight faded from discussion. Then, in 1992, Tyson went to pri–n for six years, and by the time he was out, Foreman had already cemented his legacy with his stunning knockout of Michael Moorer at age 45.

The fight that could’ve been one of the most legendary in heavyweight history never came to be. Some say it was bad timing. Others say it was bad matchmaking. But if you ask Foreman, he’ll probably tell you: Tyson just didn’t want that smoke.

4. Roy Jones Jr. vs. Nigel Benn – Super Middleweight Fireworks

How It Almost Happened?

Back in the mid-’90s, Roy Jones Jr. was the king of the pound-for-pound list—fast, powerful, and nearly untouchable. Meanwhile, Nigel Benn was a wrecking machine in the UK, knocking people out and electrifying crowds. A fight between them? It would’ve been fireworks.

For a while, there was serious talk of a unification fight. Benn was a WBC champion, and Jones had the IBF belt. Fans wanted it, and the negotiations started gaining traction. If everything had lined up, we might’ve seen one of the most explosive matchups of that era.

Why Did It Not Happen?

Unfortunately, boxing politics, tragic circumstances, and timing ruined most of these potential showdowns. Nigel Benn vs. Roy Jones Jr. was the big one. It came close, but negotiations stalled over money and location. Jones wasn’t willing to go to the UK for the fight, and Benn wasn’t eager to travel to the U.S. Either way, Jones kept moving forward with his career, and Benn never got the chance to step in the ring with him.

5. Sugar Ray Leonard vs. Aaron Pryor – The Ultimate Showdown

How It Almost Happened?

Aaron Pryor vs. Sugar Ray Leonard was this close to happening. And honestly, it should have. Pryor was an absolute beast at 140 pounds. Fast, relentless, powerful, and completely fearless. If you’ve never seen his wars with Alexis Arguello, do yourself a favor and watch them. The man was all-action, and he wanted to fight the best.

Now, back in 1976, Pryor and Leonard were both in the mix for the Olympic team at 140 pounds. But politics came into play. Leonard was the golden boy, the star, and Pryor was convinced to drop down to lightweight. He fought his heart out, even beating a young Tommy Hearns, but fell short against Howard Davis Jr., who went on to win gold. That decision haunted The Hawk. He always believed he had Leonard’s number, and from that point on, he made it his mission to prove it.

Fast forward to the early ‘80s. Pryor had become a world champion, a knockout machine, and a serious problem for anyone in his weight class. The boxing world wanted to see him and Leonard clash, and finally, in 1982, it was about to happen. The deal was almost done. Initially, Pryor was offered $500,000, but his team negotiated it up to $750,000. TV networks were on board, the fans were hyped, and it looked like the fight would take place in the fall of ‘82. This was it—Pryor’s shot at superstardom.

Why Did It Not Happen?

Then, in the blink of an eye, it was gone. Leonard took a tune-up fight against Roger Stafford before facing Pryor. Nobody thought much of it—just a routine warm-up, right? But during the fight, Leonard suffered a detached retina. Just like that, he was out. He retired shortly after, and the Pryor fight was officially dead.

For Pryor, it was devastating. Imagine chasing one fight your entire career, finally getting it lined up, and then hearing on the radio that it’s not happening. Pryor pulled his car over and broke down in tears. He knew what was slipping away—not just a payday, but the chance to cement his name in history next to Leonard, Hearns, Hagler, and Duran.

Pryor still had his incredible wars with Alexis Arguello—battles that are still talked about today. He even ended up making more money in those fights than he would have against Leonard. But that wasn’t the point. He wanted that fight because he believed he could win, and he wanted the world to know his name the way they knew Leonard’s. We missed out on something special. And honestly? That’s what hurts the most.

Which of these unrealized boxing matchups do you think would have been the most exciting? And do you know any more of such matchups that we haven’t mentioned here? Do let us know your thoughts below.