ByKel Dansby, writer at
Kel Dansby

Conor McGregor and Floyd Mayweather are arguably the two biggest names in combat sports. Mayweather sits atop boxing's highest paid fighters of all time list, and Conor is slowly climbing up that same list in the UFC.

In just three years, McGregor has completely revamped the UFC's pay structure and has set new standards for guaranteed money, but that's just a drop in the bucket for the ever-ambitious McGregor. The looming specter of a boxing match with Floyd Mayweather has consumed McGregor. Immediately after accomplishing history at UFC 205 by becoming the first simultaneous UFC two-division champion, McGregor set his course towards a "billion dollar fight" against the pseudo-retired Mayweather.

The fight had been teased since 2015, but for the first time, there was an actual possibility of bringing the match to fruition. Both McGregor and Mayweather would seize the opportunity and use Conor's platform to put the wheels in motion.

Here we sit, in February of 2017, and the Mayweather-McGregor fight seems more of a "when" rather the the previously assumed "if."

How did we go from a fight everyone scoffed at two years ago to a relative certainty?

Let us take you on a journey through the complete history of Floyd Mayweather vs Conor McGregor.

April 15th, 2015

During an interview with Esquire's Chris Jones, Conor McGregor first alludes to the possibility of fighting Floyd Mayweather.

"I don't look at a man who's expert in one area as a specialist,I look at him as a rookie in ten other areas," said McGregor.

"If you can box, what happens if I grab hold of your legs? If you put me face-to-face with Floyd Mayweather—pound-for-pound boxing's best—if I fought Floyd, I would kill him in less than thirty seconds. It would take me less than thirty seconds to wrap around him like a boa constrictor and strangle him."

April 17th, 2015

TMZ Sports reported Mayweather dismissed Conor McGregor at the time.

"Floyd "scoffed" when he saw the quotes and said, 'I don't take that dude seriously. He's just trying to get himself some publicity,'" said TMZ's sources.

August 15th, 2015

In an interview with The Guardian's Donald McRae, Conor McGregor opened up about his desire to fight Floyd Mayweather, but at the time, he lobbied for an MMA fight.“I’d also jump in and box Mayweather. 100%," said McGregor, "What do you think would happen?"

“Yeah, but in a real fight I would dismantle him in seconds. Ronda would dismantle him in seconds – 100%. When you don’t know how to grapple you don’t stand a chance. For us, it’s like playing with a baby. People who don’t understand the sport cannot understand how vulnerable they are. There are always clinches and Ronda is a judo Olympian. She would throw Floyd on his head in a second. Me? I would knock him out. Cold.”

At this point, even McGregor doubted he'd ever get a shot at fighting Mayweather.

“Why would he take me on?” McGregor says. “But if you’re talking about a fight that could generate half a billion – it’s this one. There’s never going to be another boxing fight like this. Only a cross-style match between Mayweather and me could generate that kind of interest and revenue. So maybe it could happen. I would certainly be up for it. I am capitalising on every single opportunity. It’s a strong word, one of my favourite words: capitalise. I’m ready to capitalise on everything.”

January 4th, 2016

Mayweather addresses racism in combat sports with Fight Hype and uses Conor McGregor, for better or worse, as an example.

"I don’t really know the McGregor guy; never seen him fight," said Mayweather. "They say he talk a lot of trash and people praise him for it, but when I did it, they say I’m cocky and arrogant. So biased! Like I said before, all I’m saying is this, I ain’t racist at all, but I’m telling you racism still exists."

January 8th, 2016

Conor McGregor responds to Mayweather's race discussion and takes offense with being used as an example.

"Floyd Mayweather, don’t ever bring race into my success again," McGregor told TMZ. "I am an Irishman. My people have been oppressed our entire existence. And still very much are. I understand the feeling of prejudice. It is a feeling that is deep in my blood.

In my family’s long history of warfare there was a time where just having the name ‘McGregor’ was punishable by death. Do not ever put me in a bracket like this again.If you want we can organize a fight no problem. I will give you a fair 80/20 split purse in my favour seen as your last fight bombed at every area of revenue.

At 27 years of age I now hold the key to this game. The game answers to me now."

January 20th, 2016

Conor McGregor addresses the Floyd Mayweather race comments during his now infamous "El Chapo" UFC 197 press conference.

January 25th, 2016

Floyd Mayweather defends his race comments and downplays McGregor's importance in the matter.

March 8th, 2016

Floyd Mayweather discusses McGregor's loss to Nate Diaz and makes it clear that he has no interest in fighting MMA.

May 6th, 2016

The Sun reported that a fight between Conor McGregor and Floyd Mayweather had been agreed upon and that it was only a matter of time before an announcement.

“Floyd went mad after Conor said he would crush him and

knock him out in 30 seconds, he’s obsessed with making Conor eat his words," said an anonymous source to The Sun.

“Floyd is calling the shots. It’s strictly boxing and Conor will have to lose

roughly 25lbs. It was agreed in principle on May 2, but Floyd wouldn’t reveal the identity of his opponent until last night when he told friends he’ll be fighting Conor.”

Estimated fight purses were also listed among The Sun's initial report, and that led to a fiery discussion over Conor's alleged figure and the discrepancy between Mayweather and McGregor's purse.

Mayweather is set to earn at least £100 million ($144.8 million), while McGregor will have to settle for £7 million ($10.1 million).

May 6th, 2016

Conor McGregor's coach, John Kavanagh, fans the flames on the rumored McGregor vs. Mayweather match.

May 6th, 2016

UFC President Dana White discredits reports of Conor McGregor fighting Floyd Mayweather. In a brief interview with Yahoo's Kevin Iole, White made it clear that the UFC had no negotiations from anyone from Mayweather's camp.

“It’s not true; it’s just a tabloid story,” White said. “And as far as I knew, Floyd is retired and he’s been on a world-wide vacation and hasn’t even been thinking of fighting.”

May 7th, 2016

Floyd Mayweather Sr. shares details of a conversation he had with his son Floyd Maweather Jr. about Conor McGregor.

May 8th, 2016

Despite Dana White's attempt to squash McGregor-Mayweather rumors, Conor posted a photoshopped poster of a stare down between Floyd and himself on social media.

May 11th, 2016

For the first time, UFC President Dana White gives credence to the possibility of Mayweather fighting McGregor. White also makes it clear that all negotiations will have to go through the UFC.

May 13th, 2016

Mayweather tells ShoBox that the fight with Conor McGregor will happen and that it has to be a boxing match.

May 14th, 2016

Conor McGregor responds to Floyd Meather's ShoBox comments with a simple Tweet.

May 16th, 2016

Floyd Mayweather breaks down the stipulations surrounding the McGregor fight and says he'll take nothing less than $100 million guaranteed.

May 22nd, 2016

Conor McGregor opens up about the Floyd Mayweather fight during his SportsCenter interview and says he also wants $100 million for the fight.

May 23rd, 2016

Colin Cowherd makes an announces that the Mayweather and McGregor fight will happen, and cites sources close to the negotiations.

May 29th, 2016

Floyd Mayweather shares a photoshopped pic of himself and Conor McGregor, which once again raises rumors of a finalized fight.

May 30th, 2016

Conor McGregor claims victory in the battle of the fight posters in a subliminal tweet aimed at Mayweather.

August 12th, 2016

Conor McGregor calls Floyd Mayweather a novice and says he plans to dominate both [boxing and MMA] worlds.

August 12th, 2016

Conor McGregor says Floyd Mayweather is "running around the Showtime offices begging for those executives to come up with $100 million to fight me."

November 15th, 2016

Floyd Mayweather gets fed up with the Conor McGregor comparisons and says that McGregor is an ant to his [Mayweather's] elephant.

November 15th, 2016

Conor McGregor responds to Floyd Mayweather saying he didn't watch UFC 205.

November 29th, 2016

Floyd Mayweather reminds fans that he's the highest paid fighter and that he is on a different level than all other athletes.

November 30th, 2017

Conor McGregor obtains a California boxing license.

December 2nd, 2016

Conor McGregor talks about the reasoning for obtaining a boxing license and insinuates Mayweather is scared to fight him and using his vacations as an excuse.

There's a lot to lose for [Mayweather], that's why they're scrambling, 'McGregor got the boxing license!', Floyd's in the Bahamas," McGregor said. "That's okay, I'll leave them scrambling. I got some other boxing opportunities and potential opponents in mind, previous Floyd [Mayweather] opponents. I can bring in anyone in the game."

December 13th, 2016

Floyd Mayweather says Conor McGregor is "blowing smoke up everyone's a*s," during his interview with FightHype's Ben Thompson.

December 14th, 2016

Floyd Mayweather says, "I'm going to slap the s*** out of Conor McGregor when I see him," during an Instagram Live video.

December 14th, 2016

Floyd Mayweather trolls Conor McGregor on Instagram by having fans caption a video of his loss to Nate Diaz.

December 14th, 2016

Floyd Mayweather calls Conor McGregor a "little b***h" during an Instagram Live video.

December 16th, 2016

Floyd Mayweather Facetime calls Nate Diaz to talk about possible fight with Conor McGregor.

December 23rd, 2016

Dana White responds to Floyd saying he will "slap the s*** out of Conor McGregor."

December 24th, 2016

Conor McGregor doesn't take kindly to Floyd Mayweather saying that he will slap him, and leaves a very direct tweet aimed at him.

January 13th, 2017

Dana White joins The Herd with Colin Cowherd and offers Mayweather $25 million to fight Conor McGregor.

January 13th, 2017

Floyd Mayweather laughs at Dana White's offer of an even 50-50 split with Conor McGregor at $25 million per fighter.

January 16th, 2017

Floyd Mayweather takes a shot at Dana White by calling him a "small boss," alleging Dana White used to carry his bags.

January 28th, 2017

It didn't take long for the subject of Floyd Mayweather to come up at Conor McGregor's PPV Q&A session in Manchester, England. McGregor laid out his terms for a Mayweather fight and expressed his seriousness in pursuing boxing.

“I don’t give a fuck about Floyd, either,” said Mcgregor. “If you don’t want this fight, that’s no problem. Because other than the Manny Pacquiao numbers, other than the Floyd-Manny Pacquiao pay-per-view numbers, gate numbers, I hold all the numbers. So I don’t need Floyd. I do not need him.”

January 28th, 2017

Mayweather makes a surprise appearance on the Showtime boxing telecast to discuss McGregor's earlier comments.

February 14th, 2017

The Irish Sun reports that sources from McGregor's gym believe the Conor McGregor and Floyd Mayweather fight is all but final.

Conor McGregor and Floyd Mayweather have agreed a deal to fight and have both settled on their respective fees.

“The contract hasn’t officially been signed yet because of a third party hold-up but all the details have all been agreed on.

“The fight could even be announced within two weeks.”

February 14th, 2017

Floyd Mayweather denies reports that there are negotiations between him and Conor McGregor.

February 14th, 2017

Conor McGregor takes shots at Floyd Mayweather while in Las Vegas.

February 15th, 2017

Floyd Mayweather takes McGregor's bait and lists new demands to make the fight happen.

February 24th, 2017

Floyd Mayweather shows up to Showtime Boxing event on his 40th birthday and calls out McGregor on air.

February 25th, 2017

Dana White says that they are "nowhere" with the McGregor-Mayweather negotiations and that McGregor's next fight will be in the UFC.

February 27th, 2017

Canelo Alvarez says the Mayweather vs. McGregor fight is a joke.

March 6th, 2017

Floyd Mayweather comes face-to-face with a hilarious Conor McGregor impersonator.

March 12th, 2017

Floyd Mayweather worries Conor McGregor is asking for too much money and that he may price himself out of a potential fight.

March 12th, 2017

Floyd Mayweather officially ends retirement for possible McGregor fight.

March 12th, 2017

A hold id placed on the T-Mobile Arena in Las Vegas, NV for potential fight.

March 12th, 2017

Dana White tells Conan that the Mayweather-McGregor fight will definitely happen.

"I do think it's going to happen," White told O'Brien. "It going to be a tough deal because there's obviously a lot of egos involved in this deal and a lot of people, so that always makes it tougher. On the flip side, there's money involved. I just don't see how it doesn't happen."

March 17th, 2017

Conor McGregor guarantees that he'll stop Floyd Mayweather and "shock the world!"

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