WWF King Of The Ring 1999 Review feat. Stone Cold Steve Austin vs. Vince McMahon & Shane McMahon

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To mark the 20th anniversary of the show, we are taking a look back at WWF King Of The Ring 1999. It didn’t quite reach the memorable heights of the previous KOTR, when The Undertaker sent Mankind flying off the roof of Hell In A Cell, but it was still a fun night, and a strong snapshot of the wild period known as the Attitude Era. At stake on June 27 1999 in the Greensboro Coliseum in Greensboro, North Carolina were the WWF Championship and even ownership of the company, but we also had to crown our next King (no pun intended), so let’s get to it!

WWF King Of The Ring 1999

King Of The Ring 1999 Tournament Quarter-Final Match
Hardcore Holly vs. X-Pac

Opening proceedings were two of the most recognisable mid-carders from the Attitude Era, and in a past life (well nearly four ½ years earlier), these two actually reigned as World Tag Team Champions with one another, albeit for 24 hours. Nope, short title runs weren’t just a thing under Vince Russo’s watch. I mention all this because this first PPV bout of the night wasn’t particularly noteworthy, ending abruptly after Holly whacked Pac with a steel chair. Road Dogg, the other sole remaining member of DX at that time, made a post-match rescue, but X was still hurting. At least he got to advance in the tournament, while Holly would claim he did whatever he felt like doing, even if that meant getting disqualified and missing out on the chance to win KOTR.

King Of The Ring 1999 Tournament Quarter-Final Match
Big Show vs. Kane

In later years, these two would become more closely associated than Marty Jannetty and a P45, but back in June 1999, Show was still new to the WWF, which made this their first televised singles showdown. It was your typical big man showdown, which is fine by the way; who is expecting a chain wrestling match between these two? (Actually we did get technical exchanges between the behemoths in a future Raw encounter, so I guess I stand corrected). Holly made another appearance here with a chair in hand but was stopped in his tracks, but Kane (debuting some slightly new gear here, with a bit of flesh appearing on his one-sleeve top) used the chair himself to wallop Show with, while the referee was taking a nap, to pick up the victory and advance in the competition. Kane was a babyface here, by the way.

King Of The Ring 1999 Tournament Quarter-Final Match
Billy Gunn vs. Ken Shamrock

Ken entered this match with an injury inflicted by recently-turned heel Steve Blackman on Heat, which had him coughing up blood. Billy, who had taken to being referred to solely as Mr. Ass by this stage (yep), took full advantage of the weakness, as he looked to knock off the previous KOTR winner. Shamrock attempted to fight back, as any valiant UFC-experienced babyface would be obliged to do, but referee Teddy Long insisted on stopping the match to make a tag team bout. Nah, he actually called a halt because Shamrock couldn’t continue, giving Billy Ass the win. Poor Ken.

King Of The Ring 1999 Tournament Quarter-Final Match
Road Dogg vs. Chyna

Long before the women’s revolution, one female was truly breaking barriers in the WWF/WWE. That would be Chyna, and here the Ninth Wonder Of The World was becoming the first lady to compete in the KOTR tournament. Her opponent was former DX compadre Road Dogg, but with her main man Triple H at ringside, the odds were surely in her favour to advance. That wouldn’t be the case, as Dogg took the very wise decision (and I believe he was the only man to ever do this opposite Chyna) of stuffing a metal cup down his pants.

This meant that when Chyna went for a traditional low blow, it hurt her arm far more than it pained Roadie, who then executed a Pump Handle Slam to progress and earn a scrap with his buddy X-Pac. Commissioner Shawn Michaels helped out by sending HHH backstage shortly before the finish, and both would appear again later in the show.

Edge & Christian vs. The Hardy Boyz

Though all four are bona fide legends nowadays, these two squads were still finding their way during the summer of 1999. This match, their first of many PPV battles, was an important step forward, and while it wasn’t as famous as their Ladder match later in the year at No Mercy, it was still one of the best of the entire show. Edge had the crowd on its feet when he Speared Jeff Hardy in mid-air, who had leapt off brother Matt’s back. In the end, the contest (which was a rematch from Sunday Night Heat, one spoiled by the involvement of The Acolytes) was decided again by outside interference.

Gangrel, who was still aligned with E&C in The Brood, spat his ubiquitous red liquid (or blood if you prefer) into Edge’s eyes, causing a distraction that allowed The Hardyz to claim the pin. This earned Matt and Jeff a shot at Faarooq and Bradshaw’s titles, and they would seize the gold in a major upset, while this finish marked the beginning of the end for The Brood. Bloody hell (lame joke, I know).

King Of The Ring 1999 Tournament Semi-Final Match
Billy Gunn vs. Kane

Bad Ass had to go through hellfire and brimstone to make the final. Kane was associated with X-Pac at this time, so he was battling the DX-exiled Billy on behalf of his little buddy. The match was, like several others on this card, a Raw-esque contest, and Kane seemed to have the win in the bag. But after the referee was once again in a position of blindness as it pertained to the action, Big Show came out and whacked Kane in the skull with it, thus getting revenge from earlier tonight (Show was a babyface too incidentally, though I can fully understand why you’d be confused over his alignment). Billy then picked up the three-count on a downed Big Red Machine, thus guaranteeing he would face a former DX teammate in the last match of the tournament.

King Of The Ring Tournament 1999 Semi-Final Match
X-Pac vs. Road Dogg

The obvious outcome would be for Dogg to win, thus setting up a battle of the New Age Outlaws (continuing their feud, since they had fought at Over The Edge the previous month), but that didn’t happen because Russo wanted to book a swerve, bro. Cynicism aside, X-Pac also had a gripe with Sir Ass so it was just as logical for him to win here, and he did so by hitting an X-Factor, though his neck was still causing problems based on Hardcore “I got an idea” Holly’s earlier chairshot. The two babyfaces remained friends afterwards, which was refreshing to see at a time when face and heel turns were as frequent as a Michael Cole shill for an upcoming PPV.

WWF Championship Match
The Undertaker (C) vs. The Rock

Two months after turning babyface, The Rock had an opportunity to regain the WWF Championship here at King Of The Ring 1999 against The Undertaker, who was leading the way for the Corporate Ministry. This meant he had the devilish Paul Bearer by his side, though no other members surprisingly. Since this was 1999, the early portion of this match (coming after a Rock Bottom almost secured the gold quicker than Sheamus pinned Daniel Bryan at WrestleMania XXVIII) headed up the aisleway, before returning to the squared circle after a prolonged brawl. After yet another referee bump, Bearer produced ether, which Jim Ross assured us was dangerous. I say that because we, the viewer, couldn’t exactly smell this latest viscous liquid. Bearer then poured it on a cloth for Taker to use.

But Rock intercepted it and shoved it into Taker’s eyes! That set up Rock for the win, only for HHH to come back out and Pedigree Rock. Meanwhile, JR casually said “what a no-good, lousy, son of a bitch!” A subsequent Tombstone decided the match in Taker’s favour. This was fun stuff, though not a classic by any means. The result was a reminder that maybe Road Dogg was right when he said that wins and losses don’t matter. After all, look at how many major matches Rock lost in 1999 and 2000. And yet just look at what a superstar he became. Hell, look at the star he is right now.

King Of The Ring 1999 Tournament Final
Billy Gunn vs. X-Pac

Billy Gunn didn’t quite become as big a star as The Rock did. But he certainly got the big push on this night. Capitalising on both the weakened neck and general fatigue that Pac was experiencing, Gunn (also in his third match of the night, but having suffered less punishment in part because of Shamrock being injured) had control for much of the bout. X did fight back, and even hit a desperation X-Factor. But Billy proved that he had spent sufficient time using the old Create A Finisher mode by hitting a middle rope Famouser on Pac to pin him and officially become the 1999 King Of The Ring. Yes, that made him King Ass.

Gunn’s reward was to fail in a joint attempt to claim DX merchandising rights. Then, he had The Rock shove his face into a large woman’s ass (JR’s words, not mine). Finally, he would reform the Outlaws with Road Dogg as if nothing had ever transpired between the two men.

Handicap Ladder Match For Full Ownership Of The WWF
Stone Cold Steve Austin vs. Vince McMahon & Shane McMahon

Before we get to the main event, I want to defend the reveal of Vince as The Greater Power. It was a great swerve. And though some said that it didn’t make sense, I disagree (except for Vince and Shane battling on Raw). After all, Vince was such a great heel, such a masterful villain. If anybody was willing to go through everything that he had for the previous couple of months, just to get the WWF Title off of Stone Cold, it would be him. Also helping was the almost-immediate announcement of Austin as partial CEO of the company. And that set the stage for this contest.

Throughout King Of The Ring 1999, Vince and pals told us that Shane was unable to compete. Just before bell time, Vince revealed that he would have Steve Blackman as his new partner. (What a letdown that would have been). But old Commissioner Shawn was never one for refusing to compete in advertised matches. And he showed video evidence of GTV with the news that Shane was faking his supposed ailment. This meant that The Boy Wonder would have to wrestle after all. Two decades on, and Shane remains (well after leaving for more than six years) a major player in storylines.


As was the norm in 1999, Austin got an almighty pop, and he dominated the McMahons from the opening bell. This included sending them flying into the ladders that formed the structure for the aisleway. Then, Austin pulled down the entire rack of ladders onto Vince and Shane just for fun. He also drilled Shane with an elbow drop onto the announcer’s table off the midpoint of the ladder. Vince did tip Stone Cold off a ladder onto another desk. Vinnie Mac then had The Boy Wonder stand on his shoulders and reach for the briefcase.

That wouldn’t fly with the walking whoop-ass machine that was Austin 3:16 though. Indeed, Stone Cold Stunners followed for father and son. “It’s not time to make a change …” sorry, wrong father and son. The path was open for Austin to get the briefcase and win. However, the case was mysteriously elevated high out of Steve’s reach. And not once, but twice! Austin resumed pummelling Vince, but Shane tipped a ladder over with both his dad and Stone Cold on it. That allowed Shane to scurry up to the now-lowered briefcase and earn the win, thus removing Austin from power.


A middle finger from Vince was his closing statement to Stone Cold. However, the Texas Rattlesnake had the last laugh. That happened due to him regaining the WWF Title from Undertaker the next night to a record-breaking TV audience. We never did find out for sure who lifted the briefcase, though. (Big Boss Man was hinted, but never officially confirmed, as having carried out the dirty deed.) Damn you, Russo!!!

King Of The Ring 1999 Summary

Overall, King Of The Ring 1999 was a lot of fun to relive. It definitely isn’t a great show from an in-ring standpoint. But at this time, wild characters, crazy storylines and general entertainment were the priority. And certainly more so than high spots, star ratings and social media chatter. (The latter wouldn’t be a thing for at least another decade). Furthermore, many of the heavy hitters from this chapter in the history of the company were here in full flow. Granted, there are much better PPVs from this time period. But King Of The Ring 1999 remains a good example of why so many WWF fans loved the Attitude Era.