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Highway to Hell: The Top 6 Hell In A Cell Matches of All Time

As the PWP Nation gears up for WWE Hell In A Cell with it’s ‘Highway to Hell in a Cell’ series, Crazy Bill Shannon takes a look at what he considers the 6 greatest Hell in a Cell matches of all time. 

We all knew that The Undertaker and Brock Lesnar would meet for a third time. What we did NOT expect was for it to be in the Hell In A Cell. While this could very well signal the coming of the end for Undertaker, they couldn’t have booked a better match as one of his final matches. There’s a reason that ‘Taker has been in more Hell In A Cell matches than anyone else, and he will (honestly) be dominating the top 6 matches I’m about to outline for you.

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6. Undertaker vs. Edge – SummerSlam 2008

Undertaker vs Edge SummerSlam 2008

Starting the series is a Hell In A Cell match that finally made the world see Edge for what he was: A phenomenal talent. Edge had a a “lucky” break when he cashed in his MITB contract and won the WWE Title from Cena. He developed an amazing persona as the “Rated R Superstar”, but he was still missing something.

Enter The Undertaker.

While they had a wildly entertaining feud that culminated at SummerSlam inside of the Cell, Edge got the biggest thing he could ever need, credibility from the most credible superstar the world has ever seen, Undertaker. While edge would hold every title and accolade that the WWE has ever had or offered, it was this amazing feud and 5 star match with The Undertaker that made him a true WWE Legend and proved that The Undertaker, after 17 years, could still main event and hold WWE gold.

5. Undertaker vs. Brock Lesnar – No Mercy 2002

Undertaker vs. Brock Lesnar No Mercy

The first time these two met inside of the cell was almost as iconic and unforgettable as when Lesnar wipes Hulk Hogan’s blood across his chest. Brock Lesnar was tearing through all that the WWE had to offer from Hulk Hogan to The Rock. He was King Of The Ring and was currently holding the WWE Undisputed Championship.

After a series of matches, Lesnar decided to get the upper hand on Undertaker and broke his hand. To Lesnar’s near rookie surprise, Undertaker was allowed to compete. Now he’s defending the title against the greatest superstar of all time inside of a structure that was designed just for him.

The story was great, the match was superb and NO ONE expected Lesnar to not only leave with the title, but climb to the top of the cage and hold the gold up high.  Unfortunately, Undertaker could not outlast and overcome the younger, faster and more athletic Brock Lesnar. Even though Lesnar was busted open, he soon returned the favor and as a blood bath ensued, The Undertaker put the near rookie over.

4. Undertaker vs. Mankind – King Of The Ring 1998


Pop Quiz: Who won the 1998 King Of The Ring? Who was in the WWE Title match? Who did the New Age Outlaws defend the tag titles against?

You don’t know? Well, I was there live and I don’t remember either. Undertaker vs. Mankind in the Hell In A Cell was one of the most memorable matches of the attitude era. In fact, their entire history with each other is one of the greatest rivalries in wrestling. The culmination of which took place inside of the demonic cell. Well, not exactly inside of the cell.

It was unheard of to see Mankind climb to the top of the cage with Undertaker soon following. It was unprecedented to see Foley being thrown off the top of the cell and through the announce table. It was story telling at it’s finest as Foley got away from the EMTs and climbed to the top of the cage again. Even though he was knocked out by a chair as he fell to the ring from atop the steel cell, he kept fighting. The Undertaker, WWE’s most respected and demonic superstars, finally met his match. A man whom he could not keep down. Why is this number 4 instead of number 1? Because I like the next three even more.

Answers to the quiz: Ken Shamrock was the 1998 King Of The Ring, Steve Austin and Kane wrestled in a “first blood match” and the outlaws defended the tag titles against the NEW Midnight Express (Bart Gunn and Bob Holly).

3. Undertaker vs. Shawn Michaels – Badd Blood 1997

Shawn Michaels vs Undertaker HIAC

The match that started it all. It was visionary to take the steel cage, put a top on it, then make it even bigger and taller while placing it around the outside of the ring instead of on the ring. Shawn and ‘Taker had a blood feud going and it was fantastic.

The two had an amazing adventure as Shawn Michaels isn’t shy when it comes to selling and showcasing new matches, much like his WrestleMania X ladder match with Razor Ramon. The two WWE Legends had a score to settle with each other and the fans got the ultimate payoff.

The Undertaker, who is dominating this list, didn’t end up so lucky in the match. Towards the end, Paul Bearer emerged from the back with a monster by his side. A monster that ripped the cell door off of it’s hinges and destroyed The Undertaker. It was an iconic moment as I can still see the look of fear that the Undertaker actually had on his face while Jim Ross is shouting, “That has to be Kane! That has to be Kane!”

Indeed, Jim, it was Kane, The Undertaker’s monster of a brother. From bell to bell, the match was on point and a great story unfolded.

2. Triple H vs Cactus Jack – No Way Out 2000

HHH vs Mick Foley NWO

The only match on this list that doesn’t have The Undertaker in it is surrounded by a little “dirt sheet” controversy. Rumor has it that the reason Mick Foley hasn’t done much with the WWE is because Triple H was jealous. It’s reported that many wrestlers and staff peg this match to be the match that single handily made Triple H to main event powerhouse that he became known to be.

The match told one hell of a story. It was Triple H putting his WWE Heavyweight title on the line against Cactus Jack’s career. If Foley lost, he had to finally retire. Let me tell you, neither man was prepared to lose, but this amazing battle had to have just one winner.

That winner was Triple H, the loser was Mick Foley. One of my favorite Foley matches and one of my most heartbroken moments as I’m a Foley-ite through and through.  Truthfully, if you want to watch a HIAC match that pulls you to the edge of your seat and shows you what it’s like to truly tell an emotional story in that ring, this one’s for you.

Oh, so is #1 on the list…

1. Triple H vs. Undertaker – WrestleMania 28 (“End of an Era”)

Undertaker vs Triple H WM28

It’s no surprise that I label this as my all time favorite Hell In A Cell match. After losing to the Undertaker at WrestleMania 27, but leaving the Undertaker unable to walk out of the arena, the stage was set for Triple H to try and end the streak just one more time.

This time though, it was truly signaling the end of the era I grew up with. Adding Shawn Michaels in the mi as the special ref, Triple H and Undertaker finally ended the attitude and ruthless aggression eras. A match that could have only been dreamed about happened that night and it was something special and something amazing.

My friend said to me at one point: “Why is Shawn being so over dramatic?”

Because it’s Shawn Freaking Michaels!  This is the last time we would EVER see those three men together in a ring and they all gave 220%. It was a brilliant story, an amazing match, and my personal favorite Hell In A Cell to date. The ending left me with a chill down my spine and the sad realization that my era was over. As Triple H, HBK and The Undertaker all embrace on the entrance ramp before going backstage, a tear fell from my face. It was the most perfect and surreal moment that I’ve watched.

Sound off below with YOUR favorite Hell In A Cell matches!

About Bill Shannon

  • Ford Fischer

    That list is a little warped to me. I was there and on floor next to the entrance ramp for HHH vs. Undertaker and I didn’t particularly care for it. There was too much nostalgia and drama in it for me and not enough violence. But, so goes the recent Cell matches since the PG Era began. I personally think either the KOTR 98 one or HBK/Taker are close contenders for the best two ever. HHH vs. HBK was hella long and a real roller coaster ride. Edge and Taker was good minus the cheesy ending. If I did a list of the top 6:

    6. Ambrose vs. Rollins – really well built with a great Bray Wyatt cameo at the end. Not a great culmination to the feud as there was no real clear winner, but very solid.
    5. Lesnar vs. Undertaker – vicious battle with good build surrounding the idea of whether or not Taker could use the cast on his arm…which he did to great advantage!
    4. Jericho vs. HHH – a long time coming, at least two years. A little rushed in a short-term feud as they hadn’t really met much all that year (despite long feuds in 1999, 2000, and 2001)
    3. HBK vs. HHH – 45 minute barn burner between two guys that are just better enemies than friends in my opinion. This and that SummerSlam Unsanctioned Match were brutal!!
    2. Mankind vs. Undertaker – Mainly because not much of the match was held inside the Cell and Undertaker kinda dominated it for obvious reasons. Also, no build whatsoever to the match…just was another bout in their storied years long feud.
    1. HBK vs. Undertaker – pretty tough to top the first one. It was very exciting and seeing Kane for the first time as he ripped the door off was jaw-droppingly awesome.

    Too bad a lot of these Cell matches include some kind of run-in or interference as that is normally one of the two main reasons you have a Cage or Cell match. But, remember…ANYTHING can happen in WWE as they always used to say! haha