The Undertaker’s 5 Greatest Matches Inside Hell in a Cell in WWE

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Credit: WWE

#4 – 1997 Bad Blood: Undertaker vs Shawn Michaels

There’s always something special about having the first-ever match of something special. For that reason, we have to elevate this match up the rankings.

Not only that, it was an instant classic between the two contrasting styles. The brawler in the Undertaker was looking to neutralize the speed and quickness of Michaels, who was the heel who was able to take advantage of help from his D-Generation-X teammates to gain victories earlier in the feud.

This was a match where the Undertaker looked strong as he would bust open the Heartbreak Kid from the walls of the cell. It also showed how resilient Michaels was at the time and why he was the main event star of the 1990s. But one of the biggest moments of this match was not because of either man, but the debut of Kane.

Billed as the long-lost brother looking for vengeance from a house fire during their childhood, Kane walked down to the ring and hit Undertaker with the Tombstone Piledriver. This allowed Michaels to get the win.

While the two would face each other again down the road leading up to the infamous Michaels-Austin title match at WrestleMania XIV, this was the beginning of what has been a near 30-year storyline between the two known as the Brothers of Destruction.

Next: No. 3