7. Triple H defeated Cactus Jack – No Way Out (February 27, 2000)

It was Title vs. Career as Triple H put the WWE Title on the line against a familiar foe in Cactus Jack. Most of us assumed Triple H was winning, even though we knew Jack (Mick Foley) was only about 35 years old at the time. Was he going to retire? It seemed weird to retire so young, even though we had seen him take a lot of punishment. A month earlier, they had one of my favorite matches ever at Royal Rumble 2000 in which Triple H won a bloody street fight to keep the WWE Title.

This match was also great and also bloody. They kept teasing some big spot for the match because of Foley’s Hell in a Cell match in 1998 (more on that later), so people went into it thinking he was going to hurt himself because he was crazy like that. There were times when Jack nearly won, but Triple H was tough to beat. The fight escalated to the top of the cage. Hunter gave Jack a back body drop through the roof with Jack landing in the ring, which broke as he landed. It was a planned spot to help cushion the blow. Triple H won shortly after and that was the end of Cactus Jack.

While Foley did retire as a full-timer, he had another match a month later at WrestleMania and several more matches over the years. Stipulations in WWE aren’t always true! Imagine that!

6. The Undertaker defeated Edge – SummerSlam (August 17, 2008)

It was the first Hell in a Cell match in the PG era, so it was different to see one of these matches with no blood. Here’s another example of a feud that absolutely deserved to end in Hell in a Cell. They headlined WrestleMania 24 earlier in the year, had several other matches against each other, and the only way things could end was to settle it inside the demonic structure that Undertaker helped make famous.

I liked the match a lot because they tried some different things, which is something Edge was always very good at. The big spot happened as Undertaker was standing against the cell and Edge hit a Spear (his finishing move) that broke the cage open. The match ended with Undertaker getting sweet revenge on Edge by using a camera to the head, the dreaded Conchairto and even a Spear of his own. Those are all things from their history in the build-up to this match. Undertaker won the grueling, nearly 30-minute battle with a Tombstone.

After the match was over, they did a big spot where Undertaker gave Edge a Chokeslam off the ladder that broke the ring. Then the ring was lit on fire. It was a way to send Edge “to hell” so to speak while ending this rivalry once and for all.

5. Batista defeated Triple H – Vengeance (June 26, 2005)

There are a lot of fans who may not like Triple H because he didn’t put over enough people in his career as a top guy. I’m not one of those people because of feuds like this. He elevated Batista during their rivalry on Raw in the first half of 2005. Batista won the World Title from Triple H a few months earlier, the story didn’t end there, and that’s why they had to finish it inside Hell in a Cell.

It follows the familiar story, like a lot of other matches on here. The good guy (Batista) ends up putting in a dominating performance to put an end to his adversary. I liked the use of the steel steps to ramp up the physicality with Batista using them to his advantage. After Batista kicked out of a Pedigree, he hit a Spinebuster on the steps that looked brutal. The finish was cool with Triple H trying to use the sledgehammer, but Batista hit his Batista Bomb finisher to retain the World Title after 27 minutes. It put an end to their rivalry with Batista looking like a huge star after it was over.

4. Kurt Angle defeated The Undertaker, Triple H, Steve Austin, Rikishi and The Rock – Armageddon (December 10, 2000)

It’s the most unique Hell in a Cell match in WWE history because it featured six men and the man who got the first fall would leave with Angle’s WWE Title. We probably won’t see the match ever again because WWE debuted the Elimination Chamber two years later with six men inside of an even bigger cage with a roof on it, so this one will always be unique.

If you just look at the names, they are five of the biggest stars in WWE history… plus Rikishi. No offense to him, but at least he stood out in the match by taking a flat back bump off the cell onto a truck full of hay. A 400-pound man taking that bump is pretty gutsy. It was a bloody match with a lot of fun moments, particularly when Austin and Rock squared off because the crowd was going wild for it. The finish saw Austin hit a Stunner on Rock, but Angle (the underdog heel champion) got the win by covering The Rock since Triple H hit a neckbreaker on Austin. It was a big surprise that Angle left with the gold.

I recommend this to people who didn’t watch a lot of WWE in this era. The year 2000 was my favorite year in WWE history and this is one of the better matches from that year.

3. The Undertaker defeated Mankind – King of the Ring (June 28, 1998)

When people think of Hell in a Cell matches, this is probably the first match they think of. It was a special moment in wrestling history that none of us are ever going to forget. That doesn’t mean it was the best Hell in a Cell match ever, though. I think putting it top three is just about right because it was more of a spectacle than a match.

There wasn’t much of a story between Undertaker and Mankind going into the match. They were two of the top guys and had a long rivalry two years earlier. It was the second Hell in a Cell match. As Mick Foley documented in his great first autobiography in 1999 and in countless DVDs, he wanted to top what Shawn Michaels did in the first Hell in a Cell match. They battled on top of the cell, they went near the side of it and Undertaker tossed Foley off. Foley took a 20-foot fall back/shoulder first through the Spanish announce table. It is probably the most replayed spot in WWE history because of how crazy it was.

The fact that Foley continued the match after that fall was amazing and then they topped that bump with one that was even worse. They went back up the cage, a chair was up there too and Undertaker was once again in control. Undertaker gave Foley a Chokeslam that broke the top of the cage (they didn’t think the cage would break), the chair fell through, hit Foley in the face and he landed hard in the ring. It was nasty. Somehow, Foley continued and Undertaker put him away to win clean after 17 minutes, even though it should have been much shorter.

There’s no doubt that this match shortened Foley’s career because he retired as a full-timer less than two years later. It’s also the most famous match of his career and one of the most famous matches in WWE history.

2. The Undertaker defeated Triple H – WrestleMania 28 (April 1, 2012)

The “End of an Era” match took place at WrestleMania 28 in Miami with The Undertaker facing Triple H at WrestleMania for the second year in a row with the added twist that Shawn Michaels was the special referee. There was a lot of history there because Undertaker retired Michaels at WrestleMania two years earlier and Triple H was Shawn’s best friend. Did that mean Shawn would screw Undertaker out of the win to end his WrestleMania streak? I didn’t think that would happen, but it’s that possibility which led to the intrigue of this match.

I was at this match live and I’m so glad I was, even though I had palm trees blocking my view of the ring. I was upset about some of the stuff earlier in the night, such as Daniel Bryan’s 18-second loss. This show needed this match to get the crowd into it. I can remember most of the people in our section standing for the majority of the match because we knew it was the last time these three guys would be in the same match. I’ll never forget the huge spot where Undertaker took a Superkick from Michaels, then stumbled into a Pedigree from Triple H, Michaels made the count and Undertaker kicked out. Everybody was shocked, even though we all figured Undertaker was going to win.

It was physical match with a lot of cool spots that led to believable near-falls. I’ll never forget some of the crowd reactions for the spots. Eventually, Triple H had nothing left, he couldn’t even muster the strength to use the sledgehammer some more and Undertaker put him away with the Tombstone. Their performance ended with the iconic shot of the three of them on the stage, turning to the crowd and saluting us as if to say “thank you” while we cheered for them.


The Undertaker and Triple H are the two men that have been in Hell in a Cell matches the most. Of course, their only one-on-one match inside the cell is going to be in the top two. But as amazing as this match was, it couldn’t earn the top spot.

1. Shawn Michaels defeated The Undertaker – In Your House: Badd Blood (October 5, 1997)

The first Hell in a Cell match is the best one ever and I don’t know if it’s going to be topped. I think Michaels is the best in-ring performer in WWE history, his chemistry with Undertaker is incredible and they had a great story going into it. Michaels cost Undertaker the WWE Title at SummerSlam 1997 two months earlier due to an accidental chair shot. Undertaker wasn’t happy about it, sought revenge and they had a double disqualification match at Ground Zero in September 1997.

This was also around the time when Michaels formed Degeneration X with Triple H and Chyna, making that trio the top heels in the company while Undertaker was a face looking for revenge. Putting them inside of a massive cage with a roof on it was perfect for the feud because it prevented the heel (Michaels) from running away from the face (Undertaker). Easy to understand, right?

What I loved about the match is that Undertaker dominated most of  it. Michaels kept trying to get away and failed to do so. Then they did a brilliant spot where a camera man got injured, a doctor had to check on him, so Michaels bolted for the door to break free. Undertaker attacked him there, bloodied him (great bump by Michaels into the cage) and then Michaels realized he had to go up the cage to get away. He ended up on the other side of the cage, Michaels bumped off the side of the cell (about 10 feet high) and went crashing through the announce table. It was the biggest bump in WWE history at the time. It’s also the bump that Foley felt he had to top.

There wasn’t a clean finish, but so what? It was the debut of the Kane character that we heard about from evil Paul Bearer for about six months. Who can ever forget Vince McMahon’s memorable call: “That’s Gotta Be Kane!” Cheesy, sure, but it worked. Kane hit a Tombstone on Undertaker. Michaels was out of it, but he was still able to put his arm over Undertaker’s chest to win the match in a major upset. It was a total fluke that fit his heel persona.

This is one of my favorite matches ever that I’ve watched dozens of times. It’s like watching a great movie that never gets old because of what it meant to you when you first saw it. Everybody that loves Hell in a Cell needs to watch this match again because they set the template for what the match is about. Here we are nearly 20 years later and nobody has topped it. Foley’s match with Undertaker may be the most famous, but Michaels vs. Undertaker is the best.

About John Canton

John has been writing about WWE online since the late 1990s. He joined The Comeback/Awful Announcing team in 2015. Follow John Canton on Twitter @johnreport or email him at mrjohncanton@gmail.com with any comments or questions. For more of his wrestling opinions, visit his website at TJRWrestling.net. Cheap pop!