1. Undertaker vs. Big Boss Man (Wrestlemania XV, 1999)
Widely accepted as the weakest Hell in a Cell match, this encounter is a slight stain on its legacy and makes for uncomfortable viewing it was even left off the WWEs Hell in a Cell DVD. In the build-up, Undertaker stalked Vince McMahons family in an angle that would eventually lead to the Dark Wedding and Higher Power angles. Fought between two heels, this match began as a slugfest until Big Boss Man chained Taker to the Cell and began attacking him with his nightstick. Taker eventually broke free (blading quite clearly on camera) and hit him with a chair. After 10 minutes, Taker mercifully ended the match with a Tombstone. Afterwards, The Brood ran down the aisle to help raise Bossman as he was hanged from the Cell. Imagine if WWE gave Bossman the win and stopped The Streak from ever happening. In hindsight, this was possibly the right decision from their creative team. Almost all Hell in a Cell matches have been watchable and range from decent to exceptional, but this match stands on its own as one to forget.
From Chester-le-Street, with Newcastle as my spiritual home. 24 years old, I'm at Sunderland University studying for a Sports Journalism MA. It's all about football and WWE. Wordplay jokes and puns are also encouraged.
