7. The Undertaker vs. Edge – SummerSlam 2008
Edge had been a thorn in The Undertaker’s side for over a year when they wrestled at SummerSlam. It began with Edge cashing in Money in the Bank on ‘The Deadman’, stealing the World Heavyweight Championship from him. After clashing at WrestleMania, Backlash, Judgment Day, and One Night Stand, things had to be settled inside Hell in a Cell.
This was Edge’s first and only venture inside the dreaded structure and he brought his own strategy for the match. He attempted to use tables, ladders and chairs but Undertaker could not be beaten in his signature match. There was some pro wrestling wackiness afterward but that doesn’t take away from what these men did bell to bell. The Undertaker finally got his revenge on Edge and put their rivalry to rest.
6. The Undertaker vs. Triple H – WrestleMania XXVIII
The Undertaker, Triple H, and Shawn Michaels had been at war over Undertaker’s WrestleMania streak for over three years. This was the finale of their series and like a number of other entries on this list, it had to be done inside Hell in a Cell.
This match was billed as The End of an Era. Kind of hilarious considering all three men wrestled together six years later but oh well. This was the super dramatic Hell in a Cell match. Shawn Michaels struggled with whether to call the match fair or to screw the Undertaker out of the streak. This was the Undertaker’s redemption after being brutally beaten the prior year and he achieved a ridiculous 20-0 record at WrestleMania.
5. The Undertaker vs. Shawn Michaels – WrestleMania XXVI
In many ways, Shawn Michaels was The Undertaker’s greatest rival. There was really no better man than The Undertaker to end the Heartbreak Kid’s career. Many people were curious if these two could top their classic match from the year before and while they may not have surpassed it, they definitely lived up to the hype.
Michaels was desperate to defeat The Undertaker and he was willing to put his career on the line to do it. While their previous match boiled down to one mistake made by Michaels, this one was a decisive victory for The Undertaker. As ‘The Phenom’ was set to take down his opponent, Michaels defiantly slapped him as if to say “finish me”. Sure enough, Michaels was promptly Tombstoned as The Undertaker’s streak reached 18-0 in maybe the best WrestleMania main event ever.
4. The Undertaker vs. Mankind – King of the Ring 1998
This is arguably the most iconic Undertaker match ever. Determined to put on a memorable performance, Mick Foley put his body through unthinkable destruction. Within the first minutes of the match, Foley was thrown from the top of Hell in a Cell through the announce table below. It was a moment that has been and will be replayed forever.
However, that was not the end for Mrs. Foley’s baby boy. After getting off the stretcher, Foley climbed the cage again only to be chokeslammed through the top. The match is not a technical masterpiece but it is a spectacle. It is also a match that will never be seen in WWE again.