UFC Conor McGregor's first match against Dustin Poirier in 2014 was the first time the two met in their careers. The game is considered part of Connor's UFC promotion drive. Connor gained the upper hand with skill and speed, beating Diamond in the first round with TKO style.
Two years later, in 2016, Connor and Diamond met again, this time at UFC 209. The game was lightweight, and Connor tried to defend his provisional title. However, this time, he failed to do so. Diamond sent Connor to the ground with deadly wrestling skills and won the second round with professional ground control and fighting skills.
The third game between Connor and Diamond takes place in UFC 264 in 2021. The game has attracted much attention because the tensions between the two have already attracted widespread attention. At the beginning of the game, Connor tried to attack Diamond's calf with a low leg kick in the first round. Unfortunately, however, when Connor kicked at the diamond, the sole of his foot was dislocated and caused a fracture. The referee declared Diamond the winner because Connor was unable to continue the game.
Due to Conner's injury in the Diamond Battle, the pair ushered in their fourth game in December 2021. The match also attracted much attention as Connor tried to regain victory on his third encounter with the Diamond. However, the results again disappointed Connor. Diamond showed excellent skill and patience, defeating Connor technically in the second round and winning.