WWE: Ranking all 40 Hell in a Cell matches from worst to best

WWE Owner Vincent Kennedy McMahon (c) flanked by superstars The Undertaker (l) and Brock Lesnar (r) (Photo by Simon Galloway - PA Images via Getty Images)
WWE Owner Vincent Kennedy McMahon (c) flanked by superstars The Undertaker (l) and Brock Lesnar (r) (Photo by Simon Galloway - PA Images via Getty Images) /
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With WWE Hell in a Cell 2019 less than a week away, we look back at all 40 Hell in a Cell matches and rank them from worst to best.

WWE Hell in a Cell 2019 looks poised to give us two instant classics as “The Fiend” Bray Wyatt will challenge Seth Rollins for the Universal Championship while “The Boss” Sasha Banks takes on “The Man” Becky Lynch for the Raw Women’s Championship. Both matches carry a weight of their own, but what kind of legacy will they be carrying on?

With the event looming, we take a look back at every single Hell in a Cell match since Shawn Michaels and The Undertaker first stepped inside the structure back in October of 1997. In the 22 years since that first match, 45 different superstars have competed inside Hell in a Cell. The Undertaker leads the pack with most appearances (14) and most victories (8) inside the cell.

Before I get rolling, it’s important to note the criteria that come into play here. While this ranking is subjective, it takes into account the quality of the match and story it tells (including the build to the match and immediate aftermath), the impact each match has had on HIAC history, overall reception from critics and fans, memorable moments, and sheer entertainment value.

In order to properly evaluate all 40 matches, I chose to watch them all back to back. It was quite the journey, but one that’s given me a wonderfully complete perspective on Hell in a Cell and which matches stand out amongst the rest. With all of that in mind, let’s begin.

40. The Undertaker vs. Big Boss Man

When and Where: WrestleMania XV on March 28, 1999, in Philadelphia, PA

Unfortunately, the nature of a “worst to best” list is that we begin with the bottom of the barrel. It’s hard to articulate just how horrendous this match and what WWE chose to do with it truly are. Bell to bell, it’s a pretty bland exchange. Big Boss Man did his best, but the match was mediocre at best.

What puts this on the bottom of the list is the appalling decision by WWE to hang Boss Man by the neck from the cell after the match. He twitched around until he appeared to be dead, which still stands today as one of the most disgusting things WWE has ever done, a true feat considering their history.

39. WWE Championship Match: John Cena (c) vs. Alberto Del Rio vs. CM Punk vs. Dolph Ziggler vs. Jack Swagger

When and Where: Raw on November 26, 2011, in Kansas City, MO

You might be wondering how you forgot a match like this, but you’ve probably never seen this dark match main event that took place after Raw went off the air. While a fan video of the match does exist, it’s not even worth the time to find.

This only lasted about five minutes, and barely qualifies as an official Hell in a Cell match. WWE has released a clip of the match’s ending, which gives you an idea of what it could have been while still showing you that you aren’t missing anything.

38. WWE Championship: CM Punk (c) vs. Ryback

When and Where: Hell in a Cell on October 28, 2012, in Atlanta, GA

The first of two Hell in a Cell matches to involve CM Punk and Ryback came to us in 2012, and boy was it bad. Unfortunately, Ryback got over long before he was anywhere near up to the in-ring skill needed for the position he was placed in. This was deep in the record-setting reign of CM Punk, and Ryback wasn’t even close to in his league.

The match itself was bland at best and had a few weapon spots that were quickly forgotten thanks to an abysmal finish. Ryback dominated Punk and was about to hit Shell Shock for the win, only for referee Brad Maddox to hit a low blow on Ryback and count a quick pin to help Punk take the win. Yep. You heard me.

37. CM Punk vs. Ryback & Paul Heyman

When and Where: Hell in a Cell on October 27, 2013, in Miami, FL

The second of two terrible Hell in a Cell matches involving CM Punk and Ryback came at a time when Punk was resolving bitter issues with Paul Heyman. Ryback, at this point a Paul Heyman guy, was preparing to face CM Punk at HIAC. Punk won a Beat the Clock Challenge to decide the stipulation, creating this Handicap Match inside Hell in a Cell.

Of course, Heyman never actually entered the structure. He instead arrived on a scissor lift and was placed on top of the cell. Ignoring the fact that not all competitors were in the ring, they rang the bell anyway. Punk and Ryback went on to have a better overall match than they’d put together the year before, and Punk had a clean win to cap it off. Afterward, Punk scaled the cell and destroyed Heyman as well.

36. The Undertaker & Steve Austin vs. Mankind & Kane

When and Where: Raw Is War on June 15, 1998, in San Antonio, TX

The most interesting part of this match actually took place before the bell even rang. Kane and Mankind competed in a 10-team tag team Royal Rumble to earn a shot at reigning champions New Age Outlaws. Kane and Mankind defeated LOD 2000, Midnight Express (Bombastic Bob & Bodacious Bart), Headbangers, Disciples of Apocalypse (Skull & 8-Ball), The Oddities (Kurrgan & Golga), Too Much (Brian Christopher & Scott Taylor), Steve Blackman & Farooq, Taka Michinoku & Bradshaw, and Terry Funk & Scorpio.

Immediately after starting that match, running the gauntlet, and winning, they prepared to face Steve Austin and The Undertaker inside Hell in a Cell. Undertaker didn’t show at first, so Austin started brawling with his opponents on the ramp. Bearer locked himself alone inside the cell, presumably to avoid harm, only for Undertaker to come through the ring and attack him.

That week’s episode of Raw went off the air with Austin and Kane brawling on top of the cell, without having actually finished the match. Austin ultimately picked up the win after they were off TV, ending one of the wackiest and unfortunately worst HIAC matches.