1. Giant Gonzalez
WWE.comThis one had disaster written all over it from the moment the Giant Gonzalez slowly walked to the ring at the 1993 Royal Rumble and attacked Undertaker. Gonzalez was a very tall man that wasn't very muscular, so WWE made up for it by having him wear a body suit outfit that looked absolutely ridiculous even for the 1990s. Their match at WrestleMania 9 was awful. There was nothing that Gonzalez could do to make it interesting. Undertaker tried to show babyface heart to get the fans into it, but Gonzalez was unable to sell the right way or make it interesting. Then it ended via DQ thanks to Gonzalez using chloroform and it just fell totally flat. When they had the second match at SummerSlam 1993 it wasn't much better. At least it ended with a clean Undertaker win, which was with a clothesline off the top because Gonzalez was probably unable to take any other moves. The best part about it was that the feud was over. Gonzalez was out of WWE soon after. Since Undertaker had two terrible matches with him where it looked like an embarrassment to what pro wrestling is supposed to be, Giant Gonzalez is the winner of this coveted honor as the wrestler that Undertaker truly was unable to get a good match out of.