#1 The Fiend vs The Undertaker
The Undertaker being included on this list is pretty obvious. The Phenom has been in WWE for almost three decades. During those three decades, he has dug holes and collected souls.
He has faced off against so many legends—both current and future WWE Hall of Famers—and he held the longest winning streak in WWE history, with 21 straight victories at WrestleMania, which ended at WrestleMania XXX.
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The Undertaker has been the most feared Superstar in WWE for years, however, The Deadman could hang up his boots anytime soon. He could take on 'The Fiend' Bray Wyatt in a retirement match, passing the torch to the latter in the process.
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