Halloween Havoc 1990 took place on October 28, 1990 from the UIC Pavilion in Chicago, Illinois. Barry Windham, disguised as Sting, traded places with Sting during the main event, after Sid Vicious attacked him backstage during the match. Sid originally won the match after falling on top of Windham while he tried to bodyslam Vicious. Sting came out after the pin to reveal the ruse and the match was restarted.
Halloween Havoc 1994 took place on October 23, 1994 from the Joe Louis Arena in Detroit, Michigan. All of the pre-PPV matches were shown live on Main Event. The first match of the night was originally scheduled to be Harlem Heat versus The Armstrongs, but Brad Armstrong had a family emergency, and did not appear. Per the match stipulation, Ric Flair was forced to retire. If Hulk Hogan had lost, he'd lose the title to Flair and forced to retire. After the match, Hogan was attacked by a masked man who had been stalking him for months. Hogan eventually unmasked the man to reveal him as Brother Bruti. After the unmasking, Hogan was attacked by Bruti, Kevin Sullivan, and the debuting Avalanche, before Sting made the save.
Halloween Havoc 1995 took place on October 29, 1995 from the Joe Louis Arena in Detroit, Michigan. Sgt. Craig Pittman pinned VK Wallstreet after Jim Duggan hit Wallstreet with a taped fist. Duggan's interference came after Big Bubba Rogers hit Pittman with his own taped fist to knock him out. After Diamond Dallas Page entered the ring, a fake Johnny B. Badd appeared at the entranceway (played by Joey Maggs) to distract Page and allow the real Badd to sneak up on Page from behind. The Zodiac replaced Kamala, who had left WCW. Near the end of this short match, a fan hopped the barricade and entered the ring. Savage and Zodiac fought to the outside until the referee and security could escort the fan away. Meng was disqualified after The Taskmaster interfered on Meng's behalf. Brian Pillman and Arn Anderson were disqualified when Ric Flair turned on Sting. Hulk Hogan's "Hulkster" truck pushed Giant's "Dungeon of Doom" truck out of the circle for the win. This match took place on top of the nearby Cobo Hall. Although it was portrayed as live, the match was actually taped the previous night. WCW stunt co-ordinator Ellis Edwards portrayed the referee for this match, and the commentary team was joined by Bigfoot creator Bob Chandler. After the match, Hogan and The Giant began fighting, resulting in Giant (kayfabe) falling off the side of the building.
In the main event Hogan was disqualified after Hart hit the referee with the WCW World Heavyweight Championship belt. Hart then turned on Hogan by hitting him with the world title belt and became manager of the Dungeon of Doom. After the match The Yeti came to the ring and assisted Giant in hugging Hogan, so that they were both hugging Hogan at the same time. Randy Savage came to the ring to try to save Hogan, as did Lex Luger. Lex Luger turned on Savage by attacking him and then put Hogan in the Torture Rack, joining the Dungeon of Doom. The Giant took the belt from the referee after the match and left with it; Jimmy Hart later revealed that he had a clause put in the contract that the title could change hands on a disqualification, but a week later on Nitro, The Giant was stripped of the title, because the disqualification was due to Hart's interference, The title belt was later rewarded to the winner of the 3 ring 60 man Battle Royal at WCW World War 3 1995, which was won by Randy Savage.
Halloween Havoc 1996 took place on October 27, 1996 from the MGM Grand Garden Arena in Las Vegas, Nevada. Jeff Jarrett was disqualified after Ric Flair gave The Giant a low blow. Hollywood Hogan pinned Randy Savage after The Giant chokeslammed Savage to the floor; Giant then dragged an unconscious Hogan onto Savage. During the match, Miss Elizabeth interfered on Savage's behalf. Roddy Piper came out following the match to confront Hogan and make his WCW debut.
Halloween Havoc 1997 took place on October 26, 1997 from the MGM Grand Garden Arena in Las Vegas, Nevada. Alex Wright pinned Steve McMichael after Goldberg attacked McMichael, hit the Jackhammer on him, and placed Wright on top of him. After the match Goldberg was given McMichael's Super Bowl XX championship ring by Debra and then attacked Wright in the ring. Originally the match was scheduled to be McMichael vs. Jeff Jarrett, whom Debra was managing at the time. However, Jarrett did not renew his WCW contract when it expired and instead returned to the World Wrestling Federation. Since Debra was also managing Alex Wright at the time, Wright became the replacement. Ric Flair was disqualified after he tied Curt Hennig in a tree of woe, put the title belt over Hennig's head, and kicked the center plate into his face.
The match's original ending saw Scott Hall pin Lex Luger by giving him the Outsiders Edge after Syxx interfered and kicked Luger in the head while Larry Zbyszko was arguing with an interfering Eric Bischoff. He then began celebrating in the ring with Bischoff and Syxx and forced Zbyszko to raise his hand in victory. While checking on Luger, Zbyszko suspected the nWo had played a role in Hall's victory and called for a replay of the match's ending, which confirmed his suspicions. Zbyszko grabbed the ring microphone and ordered a celebrating Hall to return to the ring as the match was resuming. Hall began arguing with Zbyszko once back in the ring, and Zbyszko shoved him into a waiting Luger. Luger then placed Hall in the Torture Rack and Hall submitted. As Zbyszko called for the bell Syxx attacked him, only to be put in a gogoplata followed by a guillotine choke. Bischoff and Hall then returned to the ring and attacked Zbyszko, ending with Bischoff kicking Zbyszko in the head and Hall counting a pin. Diamond Dallas Page was counted out after a fake Sting (Hollywood Hogan) hit Page with a baseball bat. The only way to win the match was to have your opponent not answer the referee's count of 10. Roddy Piper beat Hogan by submission with a sleeper hold. Randy Savage interfered by climbing into the cage and he and Hogan beat down Piper following the match. After the match, a fan climbed into the cage and was beat up by Savage and Hogan.
Halloween Havoc 1998 took place on October 25, 1998 from the MGM Grand Garden Arena in Las Vegas, Nevada and featured a double main event. Buff Bagwell turned on Rick Steiner during the match, leaving him to win the title on his own. Scott Steiner was a substitute for Scott Hall, the other half of the tag team champions who was wrestling later that night. During the singles match between the Steiner Brothers Bagwell wearing a mask interfered with Stevie Ray's Slapjack. Kevin Nash was counted out after he hit two Jacknife Powerbombs on Scott Hall and left the ring. Bret Hart beat Sting by TKO when he put an unconscious Sting in the Sharpshooter. Hollywood Hogan pinned Warrior after Horace Hogan came out and hit Warrior with a chair. In many areas the pay-per-view was cut off after this match, so for those areas this was the last match which aired on pay-per-view. Goldberg pinned Diamond Dallas Page after a Jackhammer. This match was also shown free the next night on Nitro, due to the pay-per-view feed cutting out in many areas.
The 1998 card is infamous for featuring a widely pilloried rematch of the main event of WrestleMania VI, a 1990 pay-per-view event produced by WCW's rival the World Wrestling Federation (WWF, now WWE) in which The Ultimate Warrior had defeated Hulk Hogan for the WWF Championship. Their 1998 return bout is regarded by critics as one of the worst matches of all time.Dave Meltzer of the Wrestling Observer Newsletter awarded it a minimum score of minus five stars out of five (the lowest ever for a WCW contest), and readers of the publication voted it the worst match of the year. Readers of professional wrestling magazine Power Slam cast the same vote; editor Fin Martin called it "one of the worst matches ever held." Then-WCW announcer Gene Okerlund described the contest as a "disaster". Comparing the WrestleMania VI and Halloween Havoc 1998 bouts, Warrior stated: "It's weird that my best match ever was with Hogan, and at the same time my worst match ever was with Hogan". Hogan felt the contest was "ruined" by his botching a spot he himself devised, in which he was supposed to "burn" the Warrior with flash paper: Hogan instead lit the paper in his own face and legit burnt his mustache and eyebrows. This led to an improvised ending in which Hogan's nephew, Horace, hit Warrior with what Sports Illustrated writer Luke Winkie called "the most unsatisfying chair shot in history". Winkie also observed a lack of co-operation between the two combatants, who did not get along personally, and slammed the contest as a "passive-aggressive wankfest". Hogan unequivocally said of the failed bout, "It was my fault."
Former WCW president Eric Bischoff conceded critical opinion that Hogan vs. Warrior II was one of the worst matches in history, and admitted that it "pretty much stunk up the joint." He however dismissed the notion that he had hired Warrior solely to lose to Hogan in return for Hogan's Wrestlemania VI loss, claiming that this is "not true" and that those who hold this belief are "drinking their own Kool-Aid". Warrior, on the other hand, said: "They used [Ted] Turner's check book to buy me to come back to lose a match to Hulk [Hogan]...it was repulsive, to me, when I finally realised it. And if I would have known I never would have went back for all the money that they gave me."WrestleCrap journalist Art O'Donnell and Fin Martin of Power Slam have also disputed Bischoff's claims, the latter writing that WCW "hired Warrior at great expense in May 1998 specifically to massage the Hogan ego."
WCW ran Halloween Havoc 1998 to three-and-a-half hours, rather than the standard three; due to this, many PPV feeds ended while the main event, Goldberg vs. Diamond Dallas Page, was still underway. WCW aired the match the following night for free on Nitro. WWE journalist Kevin Powers hailed the bout as the best ever held at the Halloween Havoc event, while criticising Hogan vs. Warrior. He wrote: "It's hard to believe that thousands of pay-per-view customers missed the main event of Halloween Havoc 1998 because WCW ran out of broadcast time. By some cruel twist of fate, fans did get to watch the disastrous WrestleMania VI rematch between The Ultimate Warrior and Hulk Hogan, only to see their screens go black just as Diamond Dallas Page prepared to lock up with undefeated WCW Champion Goldberg in what was the best match in the October event's 11-year span." Luke Winkie of Sports Illustrated said of Goldberg vs. Page: "It's a great match...if more TVs carried this match maybe the Warrior/Hogan disaster would be less remembered."
Halloween Havoc 1999 took place on October 24, 1999 from the MGM Grand Garden Arena in Las Vegas, Nevada. Perry Saturn was disqualified after Ric Flair came out and hit Eddy Guerrero with a crowbar. Rick Steiner pinned Chris Benoit after Dean Malenko came out and hit Benoit with a chair. During the match Hulk Hogan lay down for Sting, allowing Sting to pin him for the win. Referee Mickey Jay stopped the match when he deemed Sid Vicious unable to continue due to excessive bleeding after Goldberg re-opened a gash on the champion's head that Sid had received earlier in the evening. Originally, Goldberg was awarded the title following the match. The following night on Nitro, Sting declared that he never agreed to defend the title and called James J. Dillon to the ring to explain. Dillon then announced the title was being vacated due to Sting's attack on referee Charles Robinson during the unsanctioned match and announced a tournament for the vacant title to conclude at the following month's Mayhem pay-per-view event.