1) Randy Couture vs. James Toney
Similar to the aforementioned one-glove showdown between Art Jimmerson and Brazilian Jiu-Jitsu expert Royce Gracie, Randy Couture absolutely obliterated former world boxing champion James Toney at UFC 118.
It took “The Natural” just over three minutes to take the striker down, wrestle him around, gain full mount and humble a cocky boxer to the tune of a nasty arm-triangle choke. The finish proved that Toney literally had nothing for Couture outside of a one-punch knockout finish.
This is probably the biggest example of matchmaking gone wrong of all time, especially considering Toney had zero experience as a professional MMA fighter, but the UFC is doing it again with the ongoing promotional integration of Phil “CM Punk” Brooks.