15 Most Boring Matches Of WWE's Attitude Era

1. The Undertaker vs. Big Boss Man - WrestleMania XV

The most boring match in the history of the Attitude Era was the WrestleMania XV Hell in a Cell match between Undertaker and Big Boss Man. The product of the budding rivalry between Undertaker's Ministry of Darkness and Vince McMahon's Corporation, the match pitted two of the best big men in wrestling history turn in the least exciting, most disappointing cell match of all time. Undertaker was clearly not at 100-percent, his body wracked with pain following two physically taxing years of main event work. Boss Man, at that point in his career, was essentially at the mercy of his opponents when it came to producing a quality bout. He needed to be carried late in his run with the company, and Undertaker was in no shape to do it. Fans in Philadelphia sat on their hands as they watched a match that had previously been the source of epic storytelling and unforgettable moments descend into an exercise in punching and kicking. Undertaker won the match, picking up another WrestleMania win, then proceeded to hang Boss Man from the cell in a moment undoubtedly meant to make up for the awful gimmick bout that preceded it.
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Erik Beaston is a freelance pro wrestling writer who likes long walks in the park, dandelions and has not quite figured out that this introduction is not for Match.com. He resides in Parts Unknown, where he hosts weekly cookouts with Kane, The Ultimate Warrior, Papa Shango and The Boogeyman. Be jealous.