3. The Undertaker vs. Shane McMahon (WrestleMania 32)
Next on our list, we once again find The Undertaker inside the Cell, only this time against the son of the Chairman, Shane McMahon, at WrestleMania 32. This high-stakes encounter took place at AT&T Stadium in Dallas, Texas, with massive stipulations on the line: a victory for Shane would grant him full control of Monday Night Raw. At the same time, an Undertaker loss would effectively end his legendary career.
The most impressive aspect of this match wasn’t its pacing, which, like the WrestleMania 17 bout, suffered from some sluggish moments, but rather its incredible endurance. Despite Shane McMahon being a non-wrestler and The Undertaker being in the last stages of his career, they put on a physical performance that lasted for more than 30 minutes.
The matchup featured plenty of brutality, including the use of objects like monitors and bolt cutters. However, the most high-stakes moment occurred when Shane McMahon climbed to the top of the 20-foot cell, attempting a massive diving elbow onto The Undertaker. But the “Deadman” moved just in time, sending McMahon crashing through the announce table alone.

That moment was a clear callback to Mankind, whom The Undertaker famously threw off the top of the cell and through a table at King of the Ring 1998. The battle between McMahon and the “Deadman” ended as a defiant Shane gestured for The Undertaker to “bring it”, only for the “Phenom” to deliver a decisive Tombstone Piledriver to seal the victory.