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#4. Khabib Nurmagomedov vs. Charles Oliveira
Another Khabib Nurmagomedov fight that never happened was Khabib vs Charles Oliveira. The current UFC lightweight champion and former champion could’ve settled the debate on who the better grappler is.
Since Nurmagomedov vacated his lightweight championship and officially retired, Oliveira has taken over the division. ‘Do Bronx’ is currently on a 9-fight winning streak and holds the record for most finishes in UFC history. Oliveira showcased his grappling in his win over Tony Ferguson and showed his resilience in his TKO win over Michael Chandler.
Oliveira would make for an intriguing matchup against Nurmagomedov. The high-level grappling of both fighters would make things interesting. Nurmagomedov had a close call in his title defense over Dustin Poirier, which saw him narrowly escape a guillotine-choke. Perhaps if it had been Oliveira in that position, he might’ve been able to hand Khabib his first career loss.
#3. Khabib Nurmagomedov vs. Max Holloway
Another fight that never ended up happening was Nurmagomedov vs Max ‘Blessed’ Holloway.
At UFC 223, Khabib was originally scheduled to fight Tony Ferguson, however, Ferguson was forced to withdraw due to an injury. The promotion looked for last-minute replacements to step in and featherweight champion Max ‘Blessed’ Holloway answered the call. Holloway was about to attempt what many felt seemed impossible. He stepped in on short-notice to fight the undefeated Khabib for a chance to become a two-division UFC champion.
Everything looked like it was going according to plan. A new poster was made and both fighters took part in an entertaining press-conference. However, plans changed once again. The commission felt Holloway wouldn’t be able to make 155lbs safely and stopped his weight-cut.
It looked like former UFC lightweight champion Anthony Pettis might step in, however that fight didn’t materialize either. Nurmagomedov still fought at UFC 223 when Al Iaquinta stepped in and the fight was set to be the new main event. Nurmagomedov defeated Iaquinta by unanimous decision to win the vacant UFC lightweight championship and remained undefeated.
