#1.)vs. Shawn Michaels – Badd Blood 1997
The first Hell in a Cell match remains timeless. It was to determine the #1 contender to Bret Hart’s WWF title – a prelude to the Montreal Screwjob. As we’ve seen in the two WrestleMania bouts, The Undertaker and Shawn Michaels had an unreal level of chemistry in the ring together. This went back as early as 1997 in their war inside the Cell.
It led to the most iconic debut in WWE history – that of Kane, who ended up making a shocking appearance and tearing open the Cell door before attacking his half-brother The Undertaker. It was the perfect debut and it protected The Undertaker, allowing Michaels to take the pin.