20. WWF WrestleMania VIII
In The Undertaker’s first major match as a Babyface, he defeated Jake “The Snake” Roberts, one of the company’s Top Heels at that time, infront of 62,000+ fans at WWF WrestleMania 8 on April 5, 1992.
19. WWF In Your House 18: Badd Blood
While this is the only match on this list that The Undertaker actually lost, this PPV match on October 5, 1997 happened to be the very first Hell in a Cell match in the History of the business and also marked the debut of the Undertaker’s evil brother Kane.
18. WWF King of the Ring 1998
When The Undertaker defeated Mankind in their Hell in a Cell match on June 28 1998, he didn’t only threw Mankind from the top of the cage onto the announce table but also chokeslammed him through the roof of the cell into the ring just a few moments later.
17. WWF Over The Edge 1999
In the Main Event of the infamous Over The Edge PPV on May 23 1999, The Undertaker defeated “Stone Cold” Steve Austin after a fast count by Special Guest Referee Shane McMahon.
This PPV was never released on VHS or DVD because of the tragic accident that ended the life of “The King of Harts” Owen Hart.
16. WWF WrestleMania X-Seven
Infront of 67,000+ Fans on April 1 2001, The Undertaker pinned “The Game” Triple H in the Co-Main Event of WWF WrestleMania 17.