On the June 1, 1998, edition of Raw is War, having spent months alternating between the characters of Dude Love and Cactus Jack, Foley would revert to the Mankind character, and formed an alliance with Kane. That night, the Undertaker and Kane had a match to determine who would be the number-one contender for Stone Cold Steve Austin's WWF championship. During the match, Mankind interfered by choking Undertaker, allowing Kane to win the match. Mankind and Kane would challenge Undertaker and Stone Cold to the second Hell in a Cell match on the June 15 episode of Raw is War, with the match ending in a no contest. This set up the double main-event for the June PPV King of the Ring; Austin and Kane in a First Blood match for the championship, while The Undertaker and Mankind would be booked for a Hell in a Cell match. The event was scheduled to take place at the Civic Arena in Pittsburgh, 25 miles (40 km) from Freedom, Pennsylvania, where Foley had trained to become a professional wrestler at Dominic DeNucci's wrestling school, bringing his career full circle.

According to WWE producer Bruce Prichard, the original plan for the PPV was for Mankind to challenge Austin for his championship, before Vince McMahon changed the direction in an attempt to be unpredictable. Subsequently, the match had little promotion or storyline building. Calaway went into the match with a fractured ankle, but was adamant he would go through with the match and stunts as planned, later saying that it was of such great importance that he "had to do it". Foley credits head-writer Vince Russo for believing in the Mankind character, giving him confidence heading into the PPV.
Before the match, Foley and fellow wrestler Terry Funk were in Stamford, Connecticut, to watch and discuss the previous year's Hell in a Cell, brainstorming ideas about how to try and top that match, with Funk saying "maybe you should let him throw you off the top of the cage".

"Yeah," I shot back, "then I could climb back up – and he could throw me off again". Man, that was a good one, and we were having a good time thinking completely ludicrous things to do inside, outside, and on top of the cage. After a while I got serious and said quietly to Terry, "I think I can do it."

When presented with the idea of throwing Foley off the top of the cage, Calaway was hesitant, going as far as to ask Foley, "Mick, do you want to die?" Writing in his autobiography Have a Nice Day: A Tale of Blood and Sweatsocks, Foley recalls being asked by Calaway about why he wanted to execute the plan, and his response being, "I'm afraid this match is gonna stink. You can't walk, and, let's face it, I don't have any heat. We've got a heck of a legacy to live up to, and I don't want this match to ruin it. If we can start it out hot enough, we can make peopl…

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Mankind came out first and once he reached the cell, he threw a steel folding chair on top of the structure and began to climb to the top. The Undertaker then made his entrance, and followed Mankind by climbing to the top. Once on top of the cell, Foley considered aborting the planned stunt, but quickly changed his mind, later telling Ross he "wanted to create a moment" for the fans. The pair began exchanging punches and moved towards the edge of the cell. Then, in an "unbelievable moment", The Undertaker grabbed Mankind from behind and threw him from the top of the structure, propelling him 22 feet (6.7 m) through the air, sending him crashing through the Spanish commentators' table and landing on the concrete floor of the arena, which triggered Ross to famously shout, "Good God almighty! Good God almighty! They've killed him!" and "As God as my witness, he is broken in half!" Ross later said his reactions were real, and Calaway said he experienced an out-of-body experience in the moment, visualizing himself watching Mankind fly off the cage. It was seen as extra surprising as stunts involving announcers' tables are usually telegraphed by a performer removing bulky CRT monitors to protect the recipient.

Mankind remained motionless underneath the broken table, while The Undertaker remained on top of the cell. Medical personnel came out to check on Foley, as did Funk and various others, including McMahon who broke kayfabe by looking legitimately worried about someone his Mr. McMahon character was supposed to dislike. Mankind was placed on a stretcher and began to be wheeled out of the arena. However, Mankind got up from the stretcher and fought off the officials, to climb again onto the top of the cell, with The Undertaker doing likewise. After a brief brawl, The Undertaker performed a chokeslam on Mankind which sent him through the panel of the chain-link cage. The steel chair would also fall through, hitting Mankind as it landed, knocking out several teeth and knocking him unconscious; it was the first time in his career that he had been legitimately knocked out during a match. On commentary, Ross said "Good God... good God! Will somebody stop the damn match? Enough's enough!", while color commentator Jerry Lawler added, "That's it. He's dead".

According to Foley, Calaway and Prichard, the second bump through the cell roof was completely unplanned, Calaway would later say that he thought Foley was legitimately dead following the second fall, and asked Funk to check if he was still alive, while Foley would describe Ross' commentary as "not part of a wrestling match, but a legitimate cry for my well-being". Foley later said that the only reason he survived the fall was because he did not take the chokeslam properly, as he had been too exhausted to lift his body weight in response to the chokehold…

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Foley received a "rarely seen" standing ovation for the match. In the main event of the PPV between Steve Austin and Kane, the cage would be lowered again when both The Undertaker and Mankind interfered, as Kane won the WWF championship. The fourth Hell in a Cell match took place on Raw is War two months later, a singles match between tag team champions Mankind and Kane, concluding their alliance, with the match featuring another bump through an announce table, this time with Mankind halfway up the side of the cage.

In a 2020 interview with Wrestling Inc, Foley recalled that there was no mention of the match on the following night's Raw is War, as there was a belief that it was not a big moment due to the long history between the two wrestlers. Foley has said that although this match grew in legend, the reality was that his career remained "somewhat sluggish" for sometime afterwards until Foley further developed the Mankind character, and fans began to get behind him. Mankind would go on to become a three-time WWF Champion in the year following the match, and would be inducted into the WWE Hall of Fame on April 6, 2013, while The Undertaker would develop his 'undefeated WrestleMania streak' and win five more world championships before eventually retiring in 2020 before being inducted two years later in 2022.

Foley suffered several injuries in the match: a concussion, a dislocated jaw and shoulder, bruised ribs, internal bleeding, puncture wounds, and several teeth knocked out. After considering retirement, believing wrestling had passed him by, the match made Foley change his approach to wrestling, concluding he could not continue taking such dangerous bumps, leading his Mankind character to become a more gentle one who would later form a tag-team with The Rock (The Rock N Sock Connection) and use an anthropomorphic sock named "Mr. Socko".

Backstage after the match, McMahon said to Foley, "You have no idea how much I appreciate what you have just done for this company, but I never want to see anything like that again." Foley recalled that, after the match and still feeling the effects of the concussion, he turned to Calaway and asked "Did I use the thumbtacks?". Calaway responded sternly "Look at your arm, Mick!", at which point Foley discovered a significant number of thumbtacks still lodged in his arm. Russo was also surprised at Foley's demeanour after the match, recalling him questioning Russo about the quality of the match and if it was good as the previous Hell in a Cell. Foley wrote in his first book that his wife Collette cried during a post-match phone conversation between the two, and this made Foley strongly consider retiring from wrestling, something that Foley did eventually do on a full-tim…

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