On five different occasions, UFC tried to organise a bout between the duo, but none of their attempts failed to result in a headline meet.
If it wasn't injuries getting in the way, it was failed weight cuts, and if it wasn't failed weight cuts, it was a global pandemic.
For one reason or another, the fighting gods didn't want us to see Khabib vs Ferguson.
Despite the fight never actually happening, the beef and hatred between the two was very real, and that was highlighted in Khabib's autobiography.
The Russian's book was released in 2019, but excerpts highlighting Khabib's opinion of Ferguson have more recently come to light.
Writing in his autobiography, Khabib said he "sometimes felt gratitude" towards Ferguson, but also wanted to "punch him on the head so that he would look at life differently."
He added, as per mmainsight.com: "The possibility of finally silencing this poorly brought up dude became one of the main reasons for my returning to the cage.
"I have a set of emotions towards this guy like those that would flood the streets of Makhachkala at the age of sixteen or twenty when I saw in front of me an impudent lout who was boasting how strong he was.
"I never had missed the opportunity to thrash such a smartass and at the same time to check which of his claims about his abilities was true. So I looked at Ferguson and continue to do so with eyes full of sarcasm and anger.
"I assure you that my attitude promised nothing good for Tony."
Nurmagomedov, now helping out the younger generation, retired from mixed martial arts in 2020 with a perfect 29-0 record - including eight knockout victories.
Both individuals' performances had pundits and fans alike gasping for a head-to-head meeting, but one failed to be organised.
The former UFC lightweight division champ mostly had a harsh review of his former challenger, but he did have some kinder words about Ferguson from a sporting perspective.
Talking about the American, Khabib said: "I gradually formed a particular contempt for Ferguson as a person. To be precise — as a person.
"I think it is wrong to treat him badly from a sporting point of view; he is a fine fighter, a winner, a champion in my division for a period and the possessor of one of the longest winning streaks in the UFC.
"He is definitely a great athlete. However, a completely mediocre upbringing and the behaviour it has generated makes him sometimes merely a nonentity."
At 37 years old, it looks as though Ferguson's time in the Octagon may well be coming to an end.
The American is currently suffering a losing run of three fights and is struggling to hit the performance levels of previous years.News Now - Sport News