Early on in their careers Khabib and Conor shared a mutual respect and even expressed such admiration for each other, nobody could expect their rivalry would go on to become one of the most fierce in UFC history.
When the Irishman was a featherweight, both men exchanged pleasantries on Twitter before meeting up and taking a picture after McGregor’s win over Dustin Poirier at UFC 178 in 2014.
But that all changed amidst a hurricane of verbal abuse from McGregor after Khabib and his team confronted Artem Lobov, a friend and training partner of McGregor.
That led to McGregor’s infamous attack at the Barclays Center in Brooklyn during the UFC 223 media day.
The Irish fighter hurled a metal trolley at a bus Khabib was travelling in, which resulted in two fighters pulling out from their fights due to injuries from smashed glass.
Khabib won the lightweight title at UFC 223 and a few months later, a date with McGregor in the Octagon was set.
In the lead up to the fight McGregor went all out to insult Khabib’s religion and family as attacks became more personal, further fuelling the hate.
At the pre-fight press conference, McGregor even went after Khabib’s manager, Ali Abdelaziz, bringing his son, Noah, into it.
He also laughed off his so-called friendship with Khabib and the respect they once had.
“I’m going to put a beating on him and his glass jaw. He bought t-shirts to support my cause, a fanboy.”
McGregor tapped out in the fourth round of their heavily publicised clash and the fight remains the UFC’s highest-ever selling pay-per-view.
However, what transpired after the fight was arguably more memorable than what took place inside the cage.
Khabib jumped into the crowd and attacked Dillion Danis, a McGregor teammate who had been insulting Khabib all night. McGregor was also jumped by several of Khabib’s teammates inside the octagon.
“I do not understand how some of you can talk about what I did at the end of the fight,” Khabib said afterwards.
“Before, McGregor had talked about my religion, about my country, and about my father. He came to Brooklyn and he almost killed a couple of people, why do they have to talk about what I did today? I do not understand it.”
Khabib retired from the sport after defeating Justin Gaethje and moving to 29-0.
Since his retirement, it appears “The Eagle” has mellowed, leaving the door open for friendship with McGregor.
“Everything is possible,” said the Dagestani fighter turned promoter.
“You know, the way we quarrelled, the same way we can reconcile. I think it is possible, maybe not just now. Let’s see, time will tell.
“I did my job. I responded to him in the cage. How else can I explain to him? I can’t speak with the words he speaks. I don’t talk that dirty language.
“I told him I will show him everything on 6 October. But about friendship, it is possible. Who are we to not forgive each other when God forgives us? I can’t tell you what is impossible, but right now it is what it is.”