The 10 Worst WWE Hell in a Cell Matches of All Time

The first ever World Wrestling Entertainment Hell in a Cell match, one involving Shawn Michaels and The Undertaker, was an instant classic, a five-star thriller that is still featured in televised HIAC highlight reels. Michaels flew off the cage and crashed into a table. Kane made his WWE debut.

It's a match that holds up nearly 20 years later.

Not all of these cage encounters have, over the years, been gems. Some have been downright awful. There have been boring Hell in a Cell matches that seemed to go on and on and on, forgettable “feuds” settled inside of a cage, and matches that did the wrestlers involved and the fans who watched zero favors.

The following list counts down the 10 worst WWE Hell in a Cell matches of all time.

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10 Mark Henry vs. Randy Orton: Hell in a Cell 2011

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Orton has a reputation for being somewhat of a boring in-ring worker. Henry, the “World's Strongest Man,” is a large human being who isn't doing much of anything with pace and speed.

Put the two together, and you've got the recipe for an average-at-best match.

The truth of the matter is that this was essentially a regular match that happened to include the ring being surrounded by a cell. That cell barely played a factor in the encounter, and it wouldn't have been missed had it not been there. Henry defeated Orton via his “World's Strongest Slam” finishing move.

9 Triple H vs. Chris Jericho: Judgment Day 2002

The Hell in a Cell match on its own was fine. There have been far worse over the past 12 years, and worse HIAC matches before it. Hell in a Cell matches are supposed to be exciting and memorable, and they should be used to end blood feuds.

Triple H vs. Jericho was neither of those.

Little of note occurred during the match, and the feud leading up to it was “meh” at best. Even Triple H landing a Pedigree somewhat out of nowhere on the top of the cell for the win was unspectacular.

You'll notice that Triple H is mentioned a lot throughout this piece. That's more a comment on how many of those type of matches he has been in over the years than it is a knock on his in-ring abilities.

8 Triple H vs. Kevin Nash: Bad Blood 2003

This Hell in a Cell battle occurred during an era when Triple H was getting money for wins over his real life friends. It also happened at a time when Triple H had packed on pounds of muscle following a serious leg injury. Add in that Nash was past his prime and carrying bum knees, and this was bound to be a slow match.

Perhaps you enjoying watching two big dudes striking each other for minutes at a time. Maybe you're a fan of wrestlers bleeding during matches. Those who aren't all that interested in either can feel safe about not re-living this match.

7 CM Punk vs. Ryback: Hell in a Cell 2012

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WWE seemed to have a star in the making in Ryback in 2012. Ryback, repackaged after his NXT/Nexus days, had been given an undefeated streak, and the big man who elicited memories of former WCW superstar Goldberg had fans in arenas all over the country chanting “Feed Me More” during WWE events.

That all began to come to an end after this match. Referee Brad Maddox lent Punk a hand, helping the then WWE champion execute a roll-up on Ryback. Maddox then delivered a fast count for the pinfall. Ryback's popularity began to fall following that defeat, and it has never again been as high.

6 CM Punk vs. Ryback and Paul Heyman Hell in a Cell 2013

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Ryback and Heyman were involved, and thus this was never going to be a classic. The match was an afterthought, as it centered around whether or not Punk would get his hands on his former manager. That Punk did after he defeated Ryback, and the Straightedge Superstar hit Heyman with several cane shots before delivering his “Go to Sleep” finisher.

This match seems like it occurred in a different WWE era. A short year later and Ryback will likely never become a star babyface or a monster heel, Heyman has aligned himself with WWE Champion Brock Lesnar, and Punk has left the company. Punk has repeatedly stated that he is now retired.

5 Triple H and Shawn Michaels vs. Cody Rhodes and Ted DiBiase

It's easy for casual fans to forget that WWE once paired Rhodes and DiBiase together for the short-lived “Legacy” unit that also included Randy Orton. The Legacy feud with the D-Generation-X founders was just as memorable in that it wasn't at all. Legacy probably should have won, had the company been interested in pushing the young talent, but DX instead emerged victorious to the delight of the fans in attendance.

Much has changed since that evening. Triple H and Randy Orton are together as parts of “The Authority,” Rhodes now goes by “Stardust,” and DiBiase is no longer with WWE. So much for Legacy being the new Evolution.

4 Triple H vs. Shawn Michaels: Bad Blood 2004

Triple H and long-time friend Shawn Michaels were involved in several good matches following The Heartbreak Kid returning from a back injury in the summer of 2002. This, however, was not one of them.

The two apparently entered that night with the mission of having the longest Hell in a Cell match in WWE history. They achieved that goal, going over 40 minutes in the ring. That match makes this list partially because of its length.

Nothing spectacular or memorable occurred during the match. One guy had the advantage for some time. Then, the other man took control. Triple H went on to win a contest that isn't worth reviewing via WWE Network.

3 Mankind vs. Kane: Raw is War, August 1998

WWE was averaging one Hell in a Cell match a month in the summer of 1998. This battle featured two men who were tag team partners and Tag Team Champions when they entered the cage.

Mankind and Kane battled outside of the ring for several minutes. Kane took control of the contest when he slammed the cage door on the head/neck of his opponent. Mankind eventually fought back with the help of a steel chair, but Kane appeared to have the match wrapped up after hitting a tombstone.

The Big Red Machine wasn't done yet. Kane hit Mankind in the head with several unprotected chair shots, and Kane landed one final tombstone, this one on the surface of the chair. Steve Austin entered the ring to save the day, however, leaving fans with no winner of the match.

2 The Undertaker and Steve Austin vs. Mankind and Kane: Raw is War, June 1998

The original Hell in a Cell gimmick had two storyline purposes: To keep those not participating in the match on the outside looking in, and to serve as the conclusion of a feud after one wrestler defeated the other.

Neither of those things happened on that Monday night in 1998.

The match itself didn't even occur. Austin was beaten down by Mankind and Kane for several minutes as Paul Bearer made his way into the ring. Undertaker then rose up through the bottom of the ring to attack who was, at the time, his former manager. This Hell in a Cell “match” ended in a no contest.

1 The Undertaker vs. Big Boss Man: WrestleMania XV

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The Undertaker was one of the baddest characters in all of WWE heading into WrestleMania XV. He was the leader of the evil Ministry of Darkness. The Undertaker terrorized company chairman Vince McMahon and McMahon's family. Somebody had to step up and stop The Dead Man on wrestling's biggest stage.

The Big Boss Man wasn't the wrestler to do it.

Undertaker made quick work of Boss Man, hitting his opponent with a tombstone before making a pin in under ten minutes. Then, with the help of The Brood and Paul Bearer, Undertaker hung – yes, hung – Boss Man using a noose. WWE cared so much about this that the company aired a video package as Boss Man was taken down and stretchered off to the back.

It was a fitting ending for what was a missable affair.

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