This Is The Worst Royal Rumble Match In WWE History...
- Thomas Hall
- 1 day ago
- 7 min read

I’m not entirely sure how it’s happening but we are only a few years away from the fortieth anniversary of the Royal Rumble. While it was the last of the Big Four events to come to pay per view, it has become the second biggest show of the year, mainly on the back of its namesake match. That has made the Royal Rumble one (or two since 2018) of the most important matches of the year, as it is certainly rather unique. There have been quite a few of them over the years, but one of them stands out below all of the others in a rather negative way.
Since the initial version in 1988 (ok, initial televised version but close enough), there have been 46 Royal Rumbles (not counting special editions on TV, at house shows or the Greatest Royal Rumble, which was never a real one anyway) counting men’s and women’s editions. While some of them were amazing time capsules and showed off how good the company’s roster was at any given time. There have also been some horrible one though and this week we are looking at why one of them is the worst of the worst.
Why Do Fans Hate The 1999 Royal Rumble Match?
The year was 1999 and for those of you who remember that time, you probably remember that things were not great in wrestling. The WWF’s television content was mostly under the control of Vince Russo, who had some rather unique thoughts on how wrestling should go. To say this was not your traditional wrestling product would be an understatement and that was certainly the case with the Royal Rumble as well.
Did You Know...
So what was the big story for the Royal Rumble? Well in case you’ve been living under a rock (not the Rock mind you) for a long time, it was ALL about Steve Austin vs. Vince McMahon, which was the case for most of the year (and other years as well). The match’s big draw was to have Austin entering at #1 but McMahon entered at #2, allowing Austin to get his hands on McMahon for the first minute and a half or so. That’s exactly what happened and then... well... that’s when things go south.
Why Did Nothing Else Matter In The 1999 Royal Rumble Besides Austin Vs. McMahon?

The problem is that the match was entirely built around Austin vs. McMahon. They were there at the beginning and had to be there at the end, but you can only do that for so long without burning the two of them (and the audience) out over the course of the match. Austin vs. McMahon started the match, but that is ninety seconds out of the fifty six plus minutes that the match would run.
Now, you can have something good with Austin vs. McMahon as the focus, but that became the issue: it was the ONLY thing that felt like it mattered in the match. There was no reason to believe that anyone else was going to win the match, so not only did they have to start the match, but they had to end it as well. That’s exactly what happened, but there was quite the big break in the middle.
MORE FROM THOMAS HALL: What Makes A Great Royal Rumble Match?

While Austin and McMahon were having their brawl, they went out of the ring and brawled into the back, where McMahon’s Corporation attacked Austin. This resulted in Austin being taken out of the arena in an ambulance while McMahon, who was still in the match, came back to the arena to do commentary. Later in the match, Austin returned, eliminated a bunch of people, got distracted by the Rock, and was then eliminated by McMahon for the win.
That might sound interesting, but remember that there is over twenty eight minutes between Austin being attacked in the back and him returning (in an ambulance and passing the hearse that the Undertaker was using to kidnap Mabel, because 1999 was weird). What took place in between that time you ask? Well that’s where we get to the meat of the match and the other big problem with this thing.
Did Anyone Besides Steve Austin Or Vince McMahon Have A Real Chance To Win The 1999 Royal Rumble Match?
To put it mildly, the WWF’s roster in 1999 was... let’s call it a mixed bag. While there were certainly wrestlers who were popular, there weren’t many who felt like anything close to a threat to win the Royal Rumble. Even if you ignore how obvious it was that Austin and McMahon were the only two realistic winners of the match, let’s look at some of the names in the field. I’ll ignore some of those who were just filler and go with the biggest remaining names possible (in order of entry).
18: Kane. Yes, I had to jump all the way to number 18, as entrants 3-17 included such luminaries as Gillberg, Dan Severn, the Road Dogg, Kurrgan and Al Snow (and Edge, but he hadn’t even won his first Intercontinental Title yet so he meant nothing). That leaves us with Kane, who eliminated four people, including himself, as he was chased off by people from a mental institution. His time in the Rumble: about fifty three seconds.
19. Ken Shamrock. The reigning Intercontinental Champion and one of McMahon’s cronies... and he’s out in less than five minutes.
20. Billy Gunn. Do you see what kind of stretching I’m having to do here? Yes, Gunn was popular but a threat to win the Royal Rumble? Come on.
23. Triple H. He might be the best other option, but remember that this was still midcard Triple H, who was about seven months away from his first WWF Title and about six months away from declaring himself The Game.
30. Chyna. She won a special Royal Rumble to get the #30 spot, eliminated Mark Henry, and was gone in about thirty seconds.

Being realistic, that rounds out the top seven options to win the thing. That’s as thin of a field as you could ask for and the final four (Austin, McMahon, D’Lo Brown and the Big Boss Man) didn’t make it much better. Outside of Austin vs. McMahon, there is no one who was realistically going to win this thing and there was no way to hide that fact.
Why Was There Almost No Action During The 1999 Royal Rumble Match?
Of the thirty entrants, six of them were out in less than a minute, nine of them didn’t make it three minutes, and outside of Austin and McMahon, no one reached nineteen minutes. This was about getting people in and out as fast as they could, with two people actually mattering.
If you need any more proof that everything outside of Austin vs. McMahon didn’t matter, there are two instances which make it all but obvious. The third entrant in the match was Golga, who was eliminated in fifteen seconds. With him gone, Austin and McMahon brawled to the back, leaving the ring empty. Droz came in at #4 (and we didn’t even see his entrance) and…. stood there for about a minute and a half, waiting for Edge to come in at #5.
Later in the match, Kane eliminated himself and the ring was empty again until Shamrock came in at #19. Since he had no one to fight, he also stood there until Gunn came in at #20. Those are two stretches of just dead ring time with people standing there with nothing to do. I’m sure the fans who paid money for the tickets or the pay per view or the home video were thrilled to look at no action multiple times.
All they had to do was wait a bit with some of the eliminations and you could have had Droz vs. Golga and Kane vs. Shamrock until Edge came in. That might not be WrestleMania main event worthy, but it’s literally either that or nothing. You’re going to have some less than thrilling matches in the Royal Rumble, but I’ll take something going on over wrestlers just killing time on their own.
But that’s not what they did, as there was no reason to. The whole point of this match was Austin vs. McMahon so that was what got the attention. Why bother giving Droz or Golga or Kane or Shamrock the effort? They aren’t Austin or McMahon, so they didn’t matter in this match. It was one concept and nothing between the two of them leaving and the two of them getting together again mattered in the slightest. The people putting this together decided that it was ok to just let the crowd watch nothing because it didn’t have to do with Austin vs. McMahon. Why should I care about anything else then?
Why The 1999 Royal Rumble Match Result Ended Up Meaning Nothing?

Oh and if that’s not enough: the whole thing wound up meaning nothing anyway, because three weeks later, Austin beat McMahon in a cage match at St. Valentine’s Day Massacre to win the WrestleMania title shot anyway. In other words, after making you sit through nearly an hour of waiting for Austin vs. McMahon, you got it three weeks later and the entire Royal Rumble result was erased anyway. What fun.
There have been dozens of Royal Rumbles over the years, but most of the time, it at least felt like the matches mattered. The idea of the Royal Rumble is that anyone can win, and while that might not always feel realistic, most of the time it at least feels like there is some lip service to the idea. That was not the case in 1999, where the WWF might as well have held up a sign saying THIS ISN’T IMPORTANT, which they then doubled down on at the next pay per view. It’s the worst Royal Rumble ever and really, not much comes close.
WWE recently uplodaded the full 1999 Royal Rumble Match to their YouTube channel, WWE Vault. Check it out here:
Frequently Asked Questions About Royal Rumble 1999
Who Won The 1999 Royal Rumble Match?
Vince McMahon won the 1999 Royal Rumble by last eliminating Stone Cold Steve Austin.
Who were the final four in the 1999 Royal Rumble Match?
The final four were Vince McMahon, Stone Cold Steve Austin, D’Lo Brown, and The Big Boss Man.
How long did the 1999 Royal Rumble match last?
The match ran for 56 minutes and 38 seconds.
Who entered first and last in the 1999 Royal Rumble?
Stone Cold Steve Austin entered first while Chyna entered last.
Did the winner of the 1999 Royal Rumble main event WrestleMania XV?
No. Vince McMahon did not wrestle at WrestleMania, and Steve Austin earned the title shot later.
Where did the 1999 Royal Rumble take place?
The event was held in Anaheim, California.
Is the 1999 Royal Rumble considered the worst Royal Rumble ever?
It is widely criticized by fans and commentators and is often cited as one of the worst Royal Rumble matches of all time.
What title shot was on the line in the 1999 Royal Rumble Match?
The winner was supposed to earn a WWF Championship match in the main event of WrestleMania XV.