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#5 Khabib Nurmagomedov vs. Conor McGregor at UFC 229
One of the most controversial events that ever went down in the UFC took place at UFC 229 at the expense of Conor McGregor, Khabib Nurmagomedov, and their respective entourage.
As far as the official fight is concerned, the Dagestani phenom came into the fight as a grappling wizard, ready to display his magic. Largely dominating the first two rounds, Conor McGregor had no response to his grappling or striking.
While many argue that McGregor found his way back into the fight in the third round, it remains a dubious matter. It all came crashing down in the fourth round when 'The Eagle' took 'Notorious' down and mauled him, eventually forcing him to submit.
However, Nurmagomedov's stupefying win was marred by the unwarranted violence that went down after the fight. Khabib was seen leaping over the cage to confront Conor's entourage while the Irishman traded blows with the champion's team inside the octagon. UFC 229 is perhaps the most iconic event in UFC history and will be remembered for all the wrong reasons.
#4 Floyd Mayweather vs. Conor McGregor
The Irishman's foray into the world of boxing came against the undisputed kingpin of the sport. Call it poor luck or a masterstroke, Conor McGregor earned a lot of recognition in addition to reportedly earning a massive amount of over $100M.
McGregor started the fight strong, coming on as the aggressor in the first three rounds. Unfortunately, his conditioning that is suited to go no more than five rounds was his bane. Floyd Mayweather soon took the reins and made quick work of the Dubliner.
Towards the later stages of the fight, it was clear that 'Money' was looking to put 'Notorious' to sleep, as he had promised in the fight's buildup. Landing a flurry of shots to the Irishman's head, it was only a matter of time before McGregor was seen hugging the canvas.
As the bell sounded for the tenth round, it was clear that McGregor was running on fumes. Mayweather, capitalizing on the same, went for blood, forcing the referee to step in and save the woozy Irishman.
#3 Nate Diaz vs. Conor McGregor at UFC 196
McGregor's loss against Nate Diaz is perhaps the one that he remembers most clearly. Marking the first loss of his career in the UFC, Nate Diaz struck the Irishman like a bolt of lightning. What makes matters worse is the fact that the Stockton native took the fight on 11 days' notice.
Conor McGregor came out in the first round on the prowl for a KO. However, the fact that welterweights could eat the shots that slept featherweights hit McGregor as a rude awakening.
Relatively immune to his striking, Nate Diaz outclassed Conor McGregor on the mats as the Dubliner uncharacteristically tried his luck at a takedown in round two after being rocked. After a short tussle, McGregor offered Diaz his back which was all he needed to get a rear-naked choke. The Dubliner was forced to tap out.
