Skip to main content

Ranking Every WWF Pay Per View From 1999

Alex loves writing about WWE and critiquing their major shows.


1999 was a weird year for the company. The Federation was basically winning the Monday Night Wars, which was good because big names like Steve Austin and the Undertaker got injured. But the company did inherit big names like Paul Wight, Chris Jericho, and Kurt Angle. There was a lot of good stuff going on this year, but there was also a lot of… Let’s just say, when people make fun of the Attitude Era, they typically make fun of stuff from 99. It was also noteworthy as the year this writer became a WWF fan.

But with so many highs and lows in the company, how did that affect the PPVs? Well, there are 11 shows to talk about. Yes, 11. Besides skipping UK exclusives, Over the Edge will not be discussed here. There’s a time and place to discuss Owen Hart’s tragic death, and this article is not it.


King of the Ring

I’ve read several worst PPVs of all time lists and I’m sorry to say a lot of shows from this year pop up on them. So, picking the worst of the worst wasn’t easy. Part of me hates that I have to rank this one as Austin becoming CEO is the first angle I watched on Raw. (Even though I imagine “It was me, Austin” is when a few people stopped.)

The eponymous tournament is a big reason this show is lousy. There are lots of micro-matches and most are rubbish. Billy Gunn was one of the most baffling King of the Ring winners. I mean, having Big Show plow through the tournament seemed like such an obvious choice! Though Big Show suffers a choke from Kane that lasts to the point of hilarity. Even Chyna would have been more interesting. One of the few hidden gems is between The Brood and the Hardy Boys – a preview of much better things to come. The WWF title match between the Rock and the Undertaker sounds good on paper. But the Undertaker needed interference and even ETHER to win this. Not a good look. Steve Austin vs. Shane and Vince for control of the company was a glorified comedy match. And it’s the best match of the night. No seriously, it’s the only match worth watching. And it still has a bizarre finish.

Survivor Series

They knew Stone Cold would be unable to wrestle that night. They knew and they booked a veritable dream match anyway. As if that weren’t bad enough, the undercard was pretty bad. There was an awful women’s match with Moolah and Mae Young leading the babyfaces, a bizarre all-heel survivor series, and Big Show murdered his team of mooks so he could beat Boss Man’s team of mooks by himself. (Shame, I wanted to see Blue Meanie on a PPV.) That last one was the aftermath of the infamous Boss Man casket bit.

Kurt Angle made his official debut on this show, but he was still growing as a performer. Big Show ended up replacing Austin in the main event. Fans didn’t exactly react to this and the match felt more like an IC title match. For what it’s worth, at least WWF TRIED to provide a feel-good story. It didn’t work, but the effort was there.


Royal Rumble

Widely considered one of the worst Rumbles ever, both show and match. Before the said match, the undercard was pretty forgettable – including a lousy Sable match. Yeah, “Lousy Sable match” belongs in the Department of Redundancy Department. Though the only highlight of this show was the “I Quit” match between the Rock and Mankind. It’s a pretty wild brawl that goes all over the arena and gave the Rock a chance to show his comedy chops. But because of all the unprotected chair shots Mankind takes, this match may be hard for some people to watch (especially if you’ve seen Beyond the Mat).

There are so many reasons the Rumble match itself is hated. I lamented how the 98 Rumble centered too much on Austin, but there was at least an attempt to sell Austin as overcoming the odds. Here, the 30-man Rumble was reduced to a one-on-one feud between Austin and McMahon. The two started the match – because why beat around the bush? But there were so many guys who wouldn’t even make it to the European title in the first half. The ring was left empty on multiple occasions. There were bizarre backstage bits – including the Undertaker abducting Mabel and transforming him into Viscera. It’s bad enough that Mr. McMahon won the Rumble, but Austin looked like a complete dope in defeat. Still, as bad as this one is, compared to the King of the Ring, this at least has a so-bad-it’s-good quality. Like I can imagine someone calling this a guilty pleasure.

Also, the show created the "No Chance in Hell" theme. So there is some history.

Among other problems, Austin forgot his vest

Among other problems, Austin forgot his vest

Wrestlemania XV

It figures that a lousy Royal Rumble would beget a lousy Wrestlemania. This show had the tagline “The Raging Climax” (No innuendo there). But it’s developed the secret nickname “Russo-Mania” because so many of his tropes were on display. There were so many experiments – Road Dogg and Billy Gunn swapping title chases, two randos challenging for the tag titles. There were so many face/heel turns in one night for a few weeks of TV. And the kerfluffle over who’d referee the main event felt like a dilemma for Raw. (According to Mick Foley’s second book, it was a make-good after he was booted out of the main event.)

Not to mention, this has some of the worst matches in Mania history. Undertaker had one of his all-time stinkers in a dull affair against the Big Boss Man – that ended in a hanging! There was the final match of the infamous Brawl 4 All, where Bart Gunn was murdered by Butterbean. Then there was Tori vs. Sable – because of Tori’s inexperience, this was bad even for Sable standards. Not everything about this show is awful. X-Pac vs. Shane is one of the only decent matches – though hardly exceptional. Austin vs. the Rock was good, but they'd do better. A good main event and a happy ending probably duped people like me into thinking this show was any good.

Not a good show, but Armageddon 99 predicted the future

Not a good show, but Armageddon 99 predicted the future


Is this show good? Not really, but the booking team deserves some credit for making lemonade out of the lemons they had. Austin just left to have neck surgery. Undertaker was out (though they must have been waiting for him since he was on the poster.) It would be a month before the Radicalz debuted, and while Jericho and Angle were present, they weren’t quite ready for primetime. Though Jericho did have one of the better matches against Chyna. (He has an interesting story about it in his book.) The cage match between Kane and X-Pac was also one of the better matches.

In one of the stranger title matches in company history, Big Show beat the Big Boss Man to close out one of the most tasteless feuds ever. What should have been Big Show just destroying Boss Man, for some reason had too many rest-holds. The normally villainous Mr. McMahon played the hero and the underdog in a no-DQ match against his future real-life son-in-law. It was okay but – I can’t believe I’m saying this – Vince would have better. If people remember anything about this show (besides predicting the future), it would be The Kat winning the women’s title in a pool match. Then flashing the camera. Proof the women’s division has made leaps and bounds.



Kennel from Hell. That’s this show’s legacy. And yes, the match is as bad as people say. Even if dogs weren’t messing and loving around the ring, the match is so dull. The cell/cage combo slows this match to a crawl, and the two just bash each other with weapons and little psychology. It’s only fitting that a bad tasteless feud involving the Boss Man feeding Snow his own dog would have a bad blowoff match. Fortunately, nothing else on the show is that bad. But very little is exceptional. Like the previous show, WWF had to play with bad cards since most of the main eventers were in one match.

Honestly, people probably remember the buildup to this show more than the show itself. The six-pack challenge was the result of Mr. McMahon winning the title. Then immediately vacating it. This begot an episode of Smackdown where Triple H beat his Unforgiven opponents in their specialty matches. (Though two former ministry members filled in for 'Taker who left in that night due to injury.) In the same episode, Ken Shamrock made his final appearance, losing to Chris Jericho in a first blood match. (Check out Chris Jericho’s second book for the story of post-production fumbles and almost wearing a suit of armor.) An injury caused X-Pac to be Shamrock’s replacement (Though Shamrock still appeared in No Mercy). The match would have been better if not for a DQ-finish. See also: Jarrett-Chyna. But the DQ finish actually continued their story.

There was a face vs. face tag title match, but also a weird heel vs. heel tag match. The latter was the result of the Acolytes making sure the Dudley Boys weren’t divas like the Public Enemy. The six-pack challenge is decent – which makes sense considering the dream team of wrestlers involved. Though even that was marred by the bizarre ref strike storyline.

St. Valentine's Day Massacre

Probably the only time in history that the show sandwiched between the Rumble and Mania was better than both. There are probably others, but the gulf is pretty big. Even then, the first half of this show is a bit of a slog. After an entertaining video package where WWF footage was edited to an old-school Valentine’s song, we get Goldust vs. Bluedust – yes, one of the few PPV matches for the Blue Meanie. Al Snow and Hardcore Holly wrestling all the way to the Mississippi River was at least entertaining in a crass way. Two dull matches followed that and then a match between Ken Shamrock and Val Venis that was more entertaining for Billy Gunn trolling both guys. And Ken Shamrock loudly gave Ryan her cue to slap him.

The final leg of this show was better. Triple H and X-Pac had a decent match against Kane and Chyna. Mankind and The Rock continued their feud with an entertaining Last Man Standing Match. Yeah, the non-finish was kind of bogus. But points for the Rock randomly breaking out in song. The cage match between Steve Austin and Mr. McMahon was hardly a mat classic. But Austin beating the stuffing out of his evil boss was a fun match. And Vince began a rich history of taking bumps he’s too old for. The return of the jungle gym change should have been a big tell (especially since HHH and Kane had a cage match shortly before on Raw). But it did beget the debut of Paul Wight, a pretty big coup for the Federation.



The story of how we had a triple threat at Summerslam where Mankind won his last WWF championship is so sordid, that it probably could have been its own article: What started as Austin vs. Chyna turned into the triple threat. Mankind was only there because Austin preferred dropping the title to his buddy rather than Triple H. Jesse Ventura was mainly there because he wanted to grind his ax with WCW. Luckily, a solid match came from it.

The rest of the show was good but not great. The only stinker was a women’s title match where Ivory couldn’t carry Tori to a decent match. (Though if you want a laugh, they had a hardcore match on Raw where Tori showed she could actually be a little witty.) Tag team turmoil and Lion’s den match were alright but nothing special. Al Snow and Boss Man had an entertaining hardcore match that ended in a bar - before their feud took a severe turn for the worst. Big Show/Undertaker vs. Kane/X-Pac was a solid underdog match. The Rock infamously buried new King of the Ring Billy Gunn in a Kiss my A$# match. While most people could take the Rock’s insults and still come out fine, it doesn’t help when the fans agreed with the Rock that Gunn wasn’t ready for primetime. Surprisingly, the best match on the show was the Love Her or Leave Her match between Test and Shane McMahon. People like to make fun of him (even in death) but Test was actually pretty good. And the match combined hardcore action, high-flying, and a little comedy without being overbearing.


Fully Loaded

Having mentioned that I got into the WWF around this time, it’s nice to know there’s a show that lets me tap into my nostalgia that’s actually good. This was a big deal with the promised culmination of the Austin/McMahon feud. (Though I laugh in hindsight when I think about how I truly believed Vince would never appear on TV again.) The First Blood match was a good blowoff to the feud, playing to Austin and Undertaker’s strengths.

The undercard has its peaks and valleys. D’Lo Brown was a good worker, but he couldn’t carry Mideon to a decent match. For hardcore matches, the iron circle and Boss Man vs. Snow were pretty meh. Big Show and Kane had a much better match than their KOTR showdown – because they actually had a match and not just an extended choke. Jeff Jarrett won back his IC title from Edge – after losing it at a house show to make Edge’s hometown happy. That was a good match, as was Road Dogg and X-Pac winning the rights to the DX brand. The Rock and Triple H had a pretty good strap match – even if they had better later. Overall, one of the easiest shows from 99 to watch from start to finish.



The first Backlash had to be noteworthy as one of the few times Backlash outshined Mania. There were definitely some duds – including a surprisingly dull Undertaker/Ken Shamrock match. But there were some good ones, including a wild and somewhat gruesome Boiler Room Brawl between Mankind and Big Show. Owen Hart’s last PPV match where he and Jarrett defended their tag titles against the New Age Outlaws was decent, as was Triple H’s first big heel move against X-Pac.

In a rematch from Mania, Austin and The Rock more than topped their Wrestlemania main event. Besides being a wild brawl, the highlight is a classic moment where the Rock commandeers a camera and Austin made him pay for it. If you’ve never seen it, what happens is too good to give away. If you haven’t seen it, see it! Definitely one of their best matches. Oh, and the show ended with the so-bad-it’s good “Where to, Stephanie?”

No Mercy

Besides being a good show, it feels like the beginning of a new era. And that reason is the iconic ladder match between Edge and Christian and the Hardy Boyz (weird thinking they were still wrestling as The New Brood at the time). I don’t even know how to describe this epic match. All I can say is fans got a glimpse of the future, and the future looked good.

While this is hardly a one-match show, there were still some clunkers – mostly the first 3 matches. The Hollys vs. the New Age Outlaws and Godfather vs. Mideon were forgettable. Ivory losing her title to the Fabulous Moolah was hogwash, but at the time it did make fans happy. The Good Housekeeping match is one of the most divisive matches in company history. Some call it a joke, but I can’t help but find it entertaining – splitting the difference between so-bad-it’s-good and kind of decent wrestling. (Though anybody who knows the back story behind this one is probably surprised to see Jeff Jarrett back in Vince’s good graces.)

The Rock vs. British Bulldog is another match that people probably remember better for its buildup including lows of dog poo and highs of the Rock playing guest referee (“It doesn’t matter if the Rock counts three!”). Sadly, because of personal and drug issues, this was the last time Bulldog even sniffed the main event. Mankind vs. Val Venis is one of the weirder chapters in Mankind’s twilight years. The ladder match may have been the match of the night, but Austin and Triple H had a great Anything Goes match for the championship. Austin would leave soon for neck surgery, but his last PPV match for a while was a banger.

More Wrestling


© 2022 Alex deCourville