Antonio Rodrigo Nougeria beating Bob Sapp (Pride Shockwave)....That's right i said it. During the fight Big Nog was literally torpedoed on his head from the air by a man who outweighed him by 130 pounds and was literally getting beaten with hammer fists and getting manhandled for 2 rounds. That is until Sapp gassed and Nougeria arm barred him. Any normal MMA fighter would have been TKO'd or KO's in the first.
Rickson Gracie beating Masakatsu Funaki (Colosseum 2000) Funaki was a 2 time King of Pancrase and his record was 38-10 and was widely known in MMA circles as one of the world's best shoot wrestlers and grapplers in the world. Guy Metzger and Josh Barnett call him the best Pancrase fighter ever. Even thou Gracie came in as also known for being the best in Jiu Jitsu no one really saw him beat a top fighter and even questioned if he was was the myth was real. I had Funaki winning by TKO....Gracie won by rear naked choke, up til that time Funaki was only submitted 5 times in almost 40 fights.
Ryo Chonan beating Anderson Silva (Pride Shockwave 2004).....The match was supposed to be lopsided, However Chonan was actually winning by points but was getting hit good during round 3...when out of nowhere after getting separation enough to do a flying heel hook where in which Silva tapped. The shocking move even left Josh Barnett stunned as well as Bas Rutten who was announcing it. To this day it's still called one of the single greatest finishes in all of MMA. I still can't believe it.
Royce Gracie beating Dan Severn (UFC 4) ...Royce was outweighed in this fight by well over 90 pounds. Even thou Gracie was the winner of UFC 1 and 2 this was Gracie's biggest test. Dan Sevren was an accomplished wrestler who won just beat his previous two opponents in rather quick fashion by submissions. Severn had every advantage it seemed. For the better part of 13 minutes Gracie was on his back and seemingly unable to do much of anything as Seven was using brute strength and i gave Gracie absolutely no shot at winning against such a larger opponent. That is until out of nowhere it seemed a arm triangle formed and made Severn tap in the 15th minute, to everyone's complete shock. It was this fight that was the single most important message to the world about mixed martial arts, that the days of the larger school yard bully was over. That a smaller and even weaker opponent can win if using Jiu-Jitsu properly.