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It took Mayweather and Pacquiao far too long to fight but the pair did match up eventually in 2015, with the American winning easily on points.
He then took on McGregor two years later, with one fight and a retirement inbetween, bringing up his 50th professional victory with a tenth round stoppage.
Ever since 'Money' has stuck to his retirement, but for one exhibition fight to date, despite rumours of rematches with both Pacquiao and McGregor.
The 43-year-old is set to take on YouTuber Logan Paul next month in his latest exhibition fight and Audie Attar, who manages both Pacquiao and McGregor, reckons that's because the American knows he'd lose to both Attar's clients.
"I do believe Conor vs Floyd again, he beats him. I don't think Floyd ever takes it," the Paradigm Sports boss told Dubai Eye 103.8 Sport.
"Floyd's taking YouTubers for a paycheck right now. Floyd could take Manny Pacquiao in a rematch, you don't see him taking that fight.
"Floyd could take Conor McGregor for a rematch, you don't see him taking that fight.
"But he'll take a Logan Paul. He'll take the young Japanese fighter he fought previously.
"I think that's what he's going to do, Floyd knows he would lose if he took on either Manny Pacquiao or Conor McGregor."
Pacquiao is 42-years-old but is yet to retire from boxing and is currently the WBA (super) welterweight champion, despite not defending the title since winning it by beating Keith Thurman in July 2019.
There has been talk of him taking on Terence Crawford at some point in the future, in what would be a unification fight for the undefeated American's WBO title.
However Attar believes that a fight between his two clients is likely to happen in the future. "I definitely believe it's inevitable for 2021. Both fighters want it, that's the key," the fighters' manager added.
"You can't make something happen or orchestrate it or choreograph it - which is the buzzword of this interview - you can't fake that.
"If one side wants it and the other doesn't, it's not going to happen. But when both fighters want that fight to happen, why wouldn't it happen?
"If the fans want to see it - that almost guarantees that it's going to happen, right? As there's enough interest to develop something there."
McGregor does have a rematch in his very near future, as he takes on Dustin Poirier on January 23rd at UFC 257.
After that the Notorious could be eyeing yet another repeat opponent, as he will no doubt want Khabib Nurmagomedov to come out of retirement to face him again.
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