50. Randy Couture vs James Toney
Event: UFC 118 8/28/2010
Winning Move: Arm Triangle Choke
In UFC 1 boxer Art Jimmerson tapped out against Joyce Gracie without Gracie laying a finger on him. He said he wasn't used to the pressure of fighting off his back. Couture's submission of Toney, also a celebrated boxer, isn't spectacular in any way. It just proves the point that boxing is boxing and MMA is boxing and a bunch of other stuff.
This was Couture's easiest payday. He was gracious in victory stating, had it been a boxing match, Toney would have beaten him.