10 Biggest Ever Heel Vs. Heel WWE Matches

2. The Undertaker Vs. Kane - Judgment Day 1998

With the WWE Title vacant, Vince McMahon put the evil brother duo of The Undertaker and Kane in a match for the WWE Title with popular babyface Steve Austin as the referee. The brothers were clearly in the heel role. They were also wreaking havoc everywhere they went. The storyline reason for it made sense. They worked together to screw Austin out of the WWE Title at the PPV before this one, so now Vince put them in a match to see who the champion would be while Austin would be forced to hand over the title to the new winner. It would humiliate Austin while putting over one of Vince's guys in the scenario. As was the case a lot of time during this period, Vince's evil plans didn't work and Austin found a way around it by counting both guys down. Neither man left as WWE Champion. "And the winner of the match is Stone Cold Steve Austin!" The crowd loved it. The match was pretty boring. A lot of Undertaker's matches with Kane were. They just didn't have a great chemistry sometimes, so that's what happens. The crowd was still into it because the story was strong. It's one of the biggest heel vs. heel matches because it ended a PPV, even with the controversial finish. That show ended with the famous line from Vince McMahon: "Screw you Austin, you're fired."
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John wrote at WhatCulture from December 2013 to December 2015. It was fun, but it's over for now. Follow him on Twitter @johnreport. You can also send an email to mrjohncanton@gmail.com with any questions or comments as well.