Ranking all 25 WrestleMania matches of The Undertaker

24. The Undertaker vs. Big Boss Man – WrestleMania XV

Widely regarded as the worst Hell in a Cell match in WWE history, this WrestleMania XV encounter between The Undertaker and Big Boss Man was just very confusing from the start. At this point in time, ‘Taker was running The Ministry of Darkness, a stable that included Faarooq and Bradshaw — before they were the APA — Viscera, Mideon and The Brood, which consisted of Gangrel, Edge and Christian.

Here’s the thing with this. They were a heel stable but they got themselves involved in a program with Vince McMahon, who was the biggest heel in the world at this time, and his Corporation. They eventually kidnapped Shane McMahon, forcing Big Boss Man, who was Vince’s head of security at the time, to get involved with the feud and this match was just kind of thrown into WrestleMania XV. The Hell in a Cell stipulation was just kind of there as well. Later on, these two stables would join together as the Corporate Ministry (just awful) but not before we were treated to a terrible match.

Even the Attitude Era crowd was dead for this match. The two went back and forth for a few minutes before Boss Man handcuffed ‘Taker to the cell and beat him with the nightstick. However, those cuffs must not have been the highest of grades as The Deadman came out of them simply by falling down at one point. ‘Taker got control and would hit Boss Man with a chair and some other shots and nobody in the crowd cared one little bit.

The Undertaker would eventually hit a Tombstone for the win, thankfully ending the match after about 10 minutes. Following the win, The Brood came down to the ring and helped The Undertaker literally hang Boss Man from the cell with a noose as Paul Bearer hit the button and raised the cage. This was The Undertaker’s eighth victory at WrestleMania but easily one of his worst matches. 8-0.