The Undertaker's 23 WrestleMania Matches - From Worst To Best

21. Big Boss Man (WrestleMania XV)

The worst Hell in a Cell match ever, without a shadow of a doubt, is the dreadful Undertaker vs. Big Boss Man contest from WrestleMania XV. The first major issue with the bout is that both men were heels, thus robbing fans of anyone to invest in emotionally. Secondly, the feud was hardly deserving of Hell in a Cell. If anything, it felt like the Cell stipulation was thrown into the mix to camouflage just how crappy a match it was going to be. Luckily, fans in Philadelphia saw right through the gimmickry, booing the plodding and uninteresting match. The cage was used minimally, its purpose for existing called into question for the second time. Undertaker bled following a shot to the face with a nightstick but no 'crimson mask', weapon use or gigantic steel structure was able to rescue the match from the abyss. Two talented big men had an off night, failed to demonstrate any in-ring chemistry and the result was a pitiful match that could have doomed The Ministry of Darkness vs. The Corporation feud to failure had it not been for the later performances of The Deadman.