Mick Foley after crashing into the ring at No Way Out 2000

CinemaBlend participates in affiliate programs with various companies. We may earn a commission when you click on or make purchases via links.

Since its introduction in a number one contender match between The Undertaker and Shawn Michaels at Badd Blood: In Your House in October 1997, there have been a total of 45 grueling, brutal, and downright painful Hell in a Cell matches involving some of the biggest WWE superstars of yesteryear and today. And while not every single one of those matches has lived up to the lofty expectations set by the Phenom and the Heartbreak Kid that night in St. Louis, Missouri, many of the matches at various high-profile events, including the WWE Hell in a Cell pay-per-view, have created moments that still make wrestling fans wince in pain.

In honor of upcoming WWE Hell in a Cell event, I’ve put together a quick list of the most painful moments from the demonic structure’s history. Starting with the iconic match between The Undertaker and Mankind at King of the Ring ’98, here are the most terrifying and brutal moments in the match’s history.

The Undertaker throwing Mankind off the cell at King of the Ring 1998

The Undertaker Throws Mankind Off The Cell - King Of The Ring 1998

Leading into the 1998 King of the King tournament, The Undertaker and Mankind (one of Mick Foley’s three personas) had a shared history that went back two years earlier, but what would go down when the two WWE superstars met atop the Hell in a Cell structure that night in Pittsburgh remains the zenith of their blood feud, and the most memorable moment in the match’s history.

In the early goings of the match, before either competitor had actually entered the ring, Mankind climbed to the top of the nearly 20-foot structure, goading The Undertaker to join him. Little did anyone know but we were about to witness history when The Undertaker grabbed Mankind and tossed him off the top of the structure, with nothing but air between him and the Spanish announce table. With Jim Ross yelling “that killed him” as a semi-conscious Mick Foley is tended to by EMTs. Shockingly, the match went on...

Watch King of the Ring 1998 on Peacock.

Mick Foley after crashing into the ring at No Way Out 2000

Triple H Backdrops Cactus Jack Through The Roof - No Way Out 2000

There was no feud in early 2000 that was as heated as the one involving WWF Champion Triple H and Cactus Jack (Mick Foley’s oldest wrestling persona). Following a Street Fight at the Royal Rumble, the two bitter rivals met for a match with Foley's career on the line at No Way Out. The match, which involved multiple weapons, unprotected shots to the skull, and multiple momentum shifts, came to a climatic end when both superstars were atop the cell. When Cactus Jack attempted a piledriver, Triple H reversed into a backdrop, sending Mrs. Foley’s baby boy crashing to the ring, which partially collapsed as a result.

Watch No Way Out 2000 on Peacock.

Daniel Bryan after crashing into the cell wall at Hell in a Cell 2013

Daniel Bryan Dives Into The Hell In A Cell Wall - Hell In A Cell 2013

While not as over-the-top or bloody as Hell in a Cell matches of the Attitude Era, this emotional bout between Daniel Bryan and Randy Orton for the vacant WWE Championship at Hell in a Cell 2013 was one painful moment after another, leading to Bryan pulling off a series of suicide dives (diving between the ropes) on Orton outside the ring. The first two were successful, but the third resulted in Bryan diving headfirst into the steel structure. This is made even worse when you consider the concussion issues that would force Bryan to temporarily step away from wrestling two years later.

Watch Hell in a Cell 2013 on Peacock.

Sasha Banks after being powerbombed at Hell in a Cell 2016

Charlotte Flair Powerbombs Sasha Banks Through The Announce Table - Hell In A Calle 2016

The 2016 Hell in a Cell event was the first time two female WWE superstars had ever duked it out in the demonic structure, and the Raw Women’s Championship match between defending champion Sasha Banks and challenger Charlotte Flair made quite an impression. Before the match even officially started, the two bitter rivals put a hurting on one another, leading to Flair throwing Banks into the announce table with a powerbomb, causing the table to explode upon impact. A dazed Banks would struggle to get to her feet and was taken up the ramp on a stretcher before powering through the injury and getting to the actual start of the match.

Watch Hell in a Cell 2016 on Peacock.

Shane McMahon just before the big jump at Hell in a Cell 2017

Shane McMahon Crashes Onto The Announce Table - Hell In A Cell 2017

Shane McMahon isn’t a full-time WWE superstar but he has put his life on the line time and time again over the years to earn the affection of his father, Vince McMahon. One of the most striking examples of this came in a one-on-one match against Kevin Owens at Hell in a Cell 2017. With the former WWE Universal champion prone on the announce table, Shane O’Mac climbs to the top fo the structure, says a little prayer, and performs an elbow drop, only for Sami Zayn to pull Owens out of danger at the last second.

Watch Hell in a Cell 2018 on Peacock.

Becky Lynch placing Sasha Banks on a chair at Hell in a Cell 2019

Becky Lynch Performs A Running Dropkick On Sasha Banks - Hell In a Cell 2019

The Raw Women’s Championship match that saw Becky Lynch defend her title against Sasha Banks at Hell in a Cell 2019, despite opening the event, was the best match on the card. Clocking in at just shy of 22 minutes, this painful match had one nasty blow after another, but the biggest moment came when Lynch put on Banks on a chair that she has secured to the structure with kendo sticks.

With her opponent sitting a few feet off the ground, Becky Lynch ran along the side of the ring and performed a dropkick, bringing Sasha Banks crashing to the ground. And while not the most brutal, this is definitely the most creative moment from the match.

Watch Hell in a Cell 2019 on Peacock.

Make sure to check out the 2021 WWE Hell in a Cell Sunday, June 20, live on WWE Network on Peacock to watch the unforgiving structure’s reputation live on. In the meantime, check out CinemaBlend’s 2021 Summer TV schedule for everything else hitting the airwaves.

Up Next

Alexa Bliss' Creepy Doll Lilly And 5 Other Inanimate Objects That Have Played Huge Roles In WWE

What WWE's Drew McIntyre Thinks Of Fans Complaining About His Nonstop Bobby Lashley Matches television 13h What WWE's Drew McIntyre Thinks Of Fans Complaining About His Nonstop Bobby Lashley Matches Mick Joest
WWE Hell In A Cell: How To Watch The June 2021 Event Streaming television 15h WWE Hell In A Cell: How To Watch The June 2021 Event Streaming Philip Sledge
WWE's Vince McMahon Is Reportedly Making A Big Change To Raw And SmackDown, But Is It A Good Idea? television 24h WWE's Vince McMahon Is Reportedly Making A Big Change To Raw And SmackDown, But Is It A Good Idea? Mick Joest