Credit: WWE.com

Ranking Undertaker vs. Shawn Michaels and the Best WWE Hell in a Cell Matches Ever

Erik Beaston

Hell in a Cell returns to WWE at Bad Blood on October 5 from Atlanta, an appropriate culmination of the year-long rivalry between CM Punk and Drew McIntyre.

Though those two are greats of the industry and more than capable of delivering an all-timer, they will have their work cut out for them, thanks to a lineage of outstanding matches inside that massive, imposing, intimidating steel structure.

Ahead of their encounter at the next WWE premium live event, relive the 10 greatest matches to be held inside Hell in a Cell and find out where the original between Undertaker and Shawn Michaels, held at the In Your House: Badd Blood show in October of 1997, lands on the countdown.

10. WWE Championship Match (Armageddon 2000)

Six men battled inside Hell in a Cell at Armageddon 2000 when WWE champion Kurt Angle defended against The Rock, "Stone Cold" Steve Austin, The Undertaker, Triple H, and Rikishi. A who's who of Attitude Era icons, the match was a wild, chaotic brawl that intertwined ongoing storylines and rivalries to create one of the most star-studded main events in company history.

Angle would ultimately retain the title in his one and only appearance in the match, but it was Rikishi and Undertaker who would steal the headlines following a jaw-dropping spot that saw The American badass chokeslam the super heavyweight off the edge of the cage's roof and into the bed of a conveniently placed pickup.

The star power alone would have been enough to earn this match a spot on the countdown, but the dramatic near-falls and the expert booking when it came to weaving ongoing stories in and out of each other helped elevate the overall quality and overcome the mass of Superstars jam-packed inside the structure.

The Armageddon main event was exactly what one would want from a match with that many stars involved, at a time of great prosperity for the industry and WWE in general. It is a testament to the other nine matches in front of it that it brings up the rear at No. 10 on this countdown.

9. Jey Uso vs. Roman Reigns (Hell in a Cell 2020)

Sacrificing the big bumps and gratuitous violence for a story-heavy layout, Jey Uso and Roman Reigns rewrote the rules on what Hell in a Cell could be at the height of the pandemic era in October of 2020.

Inside the Thunderdome, they delivered an instant classic in the first-ever "I Quit" Match held the steel structure.

Uso was hellbent on proving that he could be the Tribal Chief, that he was Reigns' equal. No longer willing to be the recipient of questions from fans asking which twin he was, Jey turned in what is arguably the best performance of his career.

Ultimately, his championship hopes were dashed when Reigns applied a guillotine choke to his brother, Jimmy, forcing Jey to utter the match-ending phrase and fall in line with the The Bloodline.

A masterclass in character work, it is probably underrated, even with its place at the nine spot on this list.

8. Undertaker vs. Edge (SummerSlam 2008)

The finale of a year-long rivalry that included a WrestleMania main event, the Hell in a Cell match between The Undertaker and Edge at SummerSlam 2008 was an appropriate culmination of the hatred the two had developed for each other.

There were ladders, tables, and chairs, trademark weapons of the Rated R Superstar, as well as brawling outside of the steel structure and a spear through the announce table. Undertaker answered with a chokeslam through two tables set up back inside the cage and a Tombstone piledriver earned him the grueling, hard-fought victory.

Just to put an exclamation point on things the show went off the air with Undertaker chokeslamming his opponent through the canvas before a ring of fire engulfed the hole, indicating the heel had been driven to a hell.

A good, spot-heavy match, it was a fitting conclusion to feud with such depth and history.

7. Edge vs. Seth "Freakin" Rollins (Crown Jewel 2021)

Seth "Freakin" Rollins spent weeks in 2021 making Edge's life a living hell including breaking and entering the Hall of Famer's home, taunting him from a distance with thinly veiled threats directed at his family.

With the intensification of the hatred between them came the need for a showdown that would bring finality to their rivalry.

Enter Hell in a Cell at Crown Jewel in October 2021.

There was plenty of plunder to go around as the participants punished and tortured each other with weapons before Rollins delivered a sunset flip powerbomb through a table that would have put a lesser competitor away.

Edge recovered, used a steel pipe to apply a crossface on his opponent, then added insult to injury by delivering a stomp into a steel chair that earned him the victory.

Another match that sacrificed unnecessary risk and big bumps for narrative-driven violence, it was a reminder that Hell in a Cell can still be incredibly effective, even without guys taking big dives off the top of the structure.

6. End of an Era: Undertaker vs. Triple H (WrestleMania 28)

Four four straight WrestleManias, Undertaker, Triple H, and Shawn Michaels told an epic storyline that included two of the greatest matches of all time between The Phenom and Heartbreak Kid, and a battle of attrition between the Deadman and The Game, culminating in what was billed as "The End of An Era" inside Hell in a Cell at WrestleMania 28.

Undertaker and Triple H beat the ever-loving hell out of each other, their bodies wracked with pain and the effects of each blow apparent on their skin.

Throw in Michaels' superb performance as the special referee, amplified by his knack for the dramatic, and you have an exercise in pro wrestling storytelling that stands right alongside the most epic match-ups in industry history.

Undertaker would emerge victorious, delivering one last Tombstone piledriver to a defiant Triple H for the win.

The endearing image of the ordeal, though, came afterward when the three Superstars, giants of a bygone era, stood atop the stage and soaked in the appreciation of the fans for what was essentially a perfect match.

That is ranks outside of the top five of this list tells you everything you need to know about the quality of the wars that have taken place inside the titular structure.

5. Batista vs. Triple H (Vengeance 2005)

Credit: WWE.com

Batista had conquered Triple H in two previous encounters in 2005, including a WrestleMania main event that saw The Animal complete his meteoric rise to the top of the industry by defeating his mentor to capture the World Heavyweight Championship.

Driven by revenge and the desire to regain his title, Triple H set foot inside Hell in a Cell for a showdown with the man he hand-picked to be part of Evolution and guide to the top of the industry.

The combatants rewrote what Hell in a Cell could be, opting not to execute any big bumps from high places, they opted to bring barbarism to the steel structure, brutalizing and bloodying each other with an abundance of weapons, including a barb wire-wrapped steel chair, steel ring steps, and the challenger's trusty sledgehammer.

Ultimately, Batista overcame the focused, cerebral attack of his opponent to deliver a spinebuster onto the ring steps that drove the fight out of him and a Batista Bomb to finish off the match.

So appreciative of the efforts of both men were the fans in Las Vegas that they greeted Triple H with a standing ovation as he exited the ring.

An epic battle, it was absolutely essential to finally establishing Batista as one of the guys in WWE and a reminder that, despite his lengthy run on top of the company, The Game was still every bit as great as he claimed to be.

4. Cactus Jack vs. Triple H (No Way Out 2000)

After an extraordinary Street Fight at the Royal Rumble in January 2000 failed to settle the intensely personal rivalry between WWE champion Triple H and No. 1 contender Cactus Jack, they entered Hell in a Cell at No Way Out the following month for one final showdown in their epic feud.

Jack punished his opponent, unloading months of anger and frustration on The Game by brutalizing him in the cage, going as far as to set a barb wire-wrapped two-by-four on fire a use it on his opponent.

Triple H, as he did so many times during that fantastic 2000 run, weathered the storm and delivered a back body drop that sent Jack through the roof of the cell and the ring canvas some 20 feet below.

As Jack made it back to his feet, Triple H delivered one last Pedigree to win the match, retire his rival per pre-match stipulations, and silence anyone doubting his place at the top of the industry.

3. Cody Rhodes vs. Seth Rollins (Hell in a Cell 2022)

Cody Rhodes suffered a torn pectoral muscle leading into Hell in a Cell 2022 and the finale of his feud with Seth Rollins, but that did not stop The American Nightmare from setting foot inside the pay-per-view's titular structure.

His chest and arm nauseatingly bruised from the injury, he removed his ring jacket to an audible gasp from fans, for whom the reality of the situation was setting in.

The second-generation performer proceeded to earn the respect and adulation of the audience and his peers as he and Rollins turned in one of the greatest matches of the last 20 years.

A dramatic masterclass in grit and toughness by Rhodes, it saw him take some sickening punishment aimed directly at the torn muscle, eliciting looks of terror from fans in the arena. Instead of quitting, he powered through it and the mind games of his opponent, who wore the familiar polka dots of the "American Dream" Dusty Rhodes, and defeated Rollins with two Cross Rhodes and a shot to the face with a sledgehammer.

Today, it remains one of the gutsiest performances in WWE history and the match where the connection he had with fans became unbreakable.

2. Undertaker vs. Mankind (King of the Ring 1998)

At the 1998 King of the Ring in Pittsburgh's ominous Igloo, Mick "Mankind" Foley turned in a performance that could be characterized by some as "foolish" and others as "awe-inspiring," but was undeniably one of the most unforgettable in WWE history

First, his battle with The Undertaker started on top of the Hell in a Cell cage and seemingly concluded with him being thrown off the top of it and through the announce table below. Despite a dislocated shoulder, Mankind climbed back up the cage, only to be chokeslammed through it, crashing to the mat below. A rogue steel chair followed him down, catching him in his face and knocking him unconscious.

The match would have ended there today but the hardcore icon refused, rejoining Undertaker for the conclusion of the bout. With a tooth sticking out of his nose after it traveled his sinus cavity, Mankind managed to introduce thumbtacks, only to be driven into them by The Phenom, who ultimately put him away with the Tombstone.

The gusty performance from Foley instantly elevated his star and made him one of the faces of the Attitude Era, not to mention an industry giant that stood alongside his opponent and the likes of "Stone Cold" Steve Austin, The Rock, Kane, and Triple H as iconic members of one of the most stacked rosters of all time.

It also built on a reputation Hell in a Cell garnered right from the start, in what is still the best of its kind, less than a year earlier.

1. Undertaker vs. Shawn Michaels (In Your House: Badd Blood)

Undertaker vs. Mankind has all of the memorable moments and bumps but the best Hell in a Cell match is still that inaugural one from In Your House: Badd Blood in October of 1997.

The conclusion of Undertaker's months-long feud with Shawn Michaels, the match forced HBK to go it alone against The Phenom and the result was a bloodied, battered boy toy and a vengeful aggressor looking to end him for good.

The Deadman appeared to be well on his way to achieving his goal as he chased his opponent around the ring, out of the cell when medics assisted a cameraman, and on top of it. From there, he stomped on Michaels' hands, sending him crashing off the side of the cage and through the commentary table below.

Late in the match, an Undertaker win looked like a certainty until the lights went out and Kane made his stunning debut, stalking to the ring before coming face-to-face with his brother. A Tombstone by the masked newcomer allowed a beaten Michaels to drape a single arm over his fallen opponent and steal the win.

The narrative of the match, coupled with the physicality and violence, and topped off with one of the greatest debuts in WWE history, helped set the bar for the Hell in a Cell match. Despite some truly extraordinary performances in the 27 years since, none have perfectly encapsulated all that made the original the iconic match-up that it still is nearly three decades later.

   

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