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The two met inside the Octagon at the T-Mobile Arena in Las Vegas in October 2018 and there was huge animosity following on from McGregor's bus attack in Brooklyn, New York a few months earlier and the many below the belt jibes and insults he made to his opponent in the build-up.
The bout, which achieved a record 2.4 million pay-per-view buys, was for the lightweight title and saw Khabib make easy work of McGregor.
Although McGregor was controversially handed the third round on the judges' scorecards, the Dagestani fighter absolutely dominated 'The Notorious' and put him away with a neck crank in the fourth round.
After the fight, all hell broke loose and a wild brawl ensued. McGregor traded blows with members of Khabib's team, while 'The Eagle' jumped the Octagon and attacked Dillon Danis.
On this day, one of the biggest fights in UFC history went down at #UFC229 🔥— UFC on BT Sport (@btsportufc) October 6, 2020
Relive an unforgettable night as Khabib Nurmagomedov and Conor McGregor finally got in the Octagon together 💪 pic.twitter.com/NvNKJFVEK6
The antics were out of character for Khabib and in a recent press conference, he's detailed the depths of which he was willing to - and how things could have been even more severe if Herb Dean wasn't present.
"You saw what happened on October 6th. Remove Herb Dean and you will understand what would've happened. A person can die from a grip like that. If you want to, I can choke you behind the curtain and you'll see what would've happened," Khabib said, as per RT.
"When a person strangles you and has been doing this for 30 years, this is a cold weapon. If there had been no referee, what would've happened? Herb Dean removed my hand, he removed my grip. We understand everything. We understand what
could have been."
The bad blood between the pair has not disappeared.
Earlier this month, McGregor posted a sickening tweet about Khabib's late father Abdulmanap - writing "Covid is good and father is evil?" before deleting afterwards.
In response, Khabib branded his foe as "evil" but that only led to McGregor crossing the line again when he tweeted "I wanna eat his children!!!" in a post that he deleted but not before it was screenshotted and widely shared.
Khabib has since retired from MMA with a perfect 29-0 record and although he's been successful at coaching fighters in his team, the 32-year-old's focus is now on a football career.
He has officially become a professional footballer, signing for FC Legion Dynamo in the third tier of Russian football.