Conan O'Brien managed to drop Conor McGregor in a video game. He of course wouldn't be able to do so in a real fight and should consider it a victory to have landed a shot at all.
McGregor participated in Conan's Clueless Gamer segment and the two battled it out in UFC 2. For almost the entire segment McGregor beat the crap out of Conan.
Exactly how a fight between the two in real life would go.