5 Worst Wrestling Matches Of 1999

Sandwiched between a great year for WWE (1998) and arguably its best ever (2000) is one of the most disturbing, excessive, and discomforting years in pro wrestling history: 1999. This year was mired by absolutely awful storylines, borderline offensive gimmicks, desperate rating ploys, and the legitimate death of one of wrestling’s biggest unsung heroes: Owen Hart. Long before the tragic deaths of Eddie Guerrero and Chris Benoit, this was a moment that made many wrestling fans question the art form they were watching on a weekly basis.

As if Owen’s death wasn’t bad enough, both WWE and WCW pushed the boundaries of taste in ways that made even the staunchest of devotee question their allegiance to their respective brands. Both companies misused women in terrible ways (with Sable, in particular, being a tremendous draw but a horrible wrestler). They both put on ridiculous and offensive matches and stipulations, and in one case, an on-screen commentator openly mocked another’s a real-life illness to try and get what’s called ‘cheap heat’.

And yet, despite all of that drivel, there was actually one promotion (if you could even call it that) that actually managed to out-do both WWE and WCW in the bad match department. There was one wrestling show put on in 1999 that was so awful, and had such terrible wrestling, commentary, production and execution, that it made even the worst of WWE and WCW production look like 5-star Hollywood classic films by comparison.

So who was it? Read on to find out which companies put on the 4 worst wrestling matches of 1999.

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#5 Sable vs. Tori – WrestleMania XV

Going into WrestleMania XV, Sable (the future Mrs. Lesnar) was WWE’s Women’s Champion. Here she faced Tori in a five-minute nothing contest for the title and still managed to win, despite having minimal wrestling skill. Oh, and there’s one other problem with this match, which is a major cause of its awful rating and place on this list.

Sable had so much drawing power and backstage influence that she convinced the bookers that she would not, under any circumstances, take bumps in a match. In other words, Sable’s opponent would not take any offense or put herself in any situation that could lead to any pain whatsoever. This was despite her being in the wrestling business and trying to wrestle in a wrestling ring.

This was five minutes of painful action brought on by one woman that was relatively inexperienced and by another who refused to take even the lightest of bumps in a match. Sable shouldn’t’ve ever got into the ring if she wasn’t going to even fall on her back. It wouldn’t be until at least one year afterward that women’s wrestling in WWE would get at least slightly more exciting than this.

#4 Vampiro vs. Oklahoma – Starrcade 1999

1999 was a year during which both WWE and WCW crossed the line with bad taste in angles and gimmicks. WWE had such awful things as a wrestler being ‘hanged’ and a dog being fed to its owner, while WCW had the character Oklahoma.

Oklahoma was writer Ed Ferrara playing a hammed-up version of Jim Ross, complete with stooped face mocking JR’s real Bell’s palsy. It was an utter mockery and in horrible taste, and was made even worse by putting Okahoma in a match.

Luckily said match went just under three minutes, but it was still terrible. For some reason, WCW felt that Vampiro couldn’t beat a non-wrestler on his own in less than three minutes, so they booked a group called the Misfits to run-in and help him beat down Oklahoma, which oddly didn’t cause a disqualification.

This felt like a complete waste of time and Vampiro actually looked worse leaving this match. He couldn’t beat Oklahoma on his own and needed help; the audience must’ve seen his character as a complete weakling for that to happen.

#3 King Kong Bundy & Jim Neidhart vs. Yokozuna & Jake Roberts - Heroes Of Wrestling

This spectacular failure was brought about due to Jake Roberts being unable to control his own personal demons. The original plan was for two separate singles matches. But before Jake’s match, he cut his now-infamous ‘you wanna play 21’ promo that clearly showed that he was completely intoxicated.

By the time Roberts actually got to the ring, even further nonsense ensued. Jake was so messed up that he barely did any proper wrestling when he was actually in the ring. He spent more time ‘interacting’ with the ringside fans, standing around looking like he would fall over if he got his by the slightest breeze, and playing with his snake (literally, he pulled his python out of its bag and made suggestive actions with it which forced the camera to cut to the audience, who looked on bewildered).

By the time the singles match between Roberts and Neidhart was supposed to start, Roberts was so drunk that the promoter had to book an impromptu tag team match on the fly. Even with two more (sober) heads, the match fell apart. It was so chaotic and nonsensical that all Roberts could do was take a pin and that’s it.

This match would’ve actually been funny if it wasn’t so sad. Roberts was at arguably the lowest point of his life at this point, so it’s heartwarming to see that he has actually made a comeback in more recent years.

#2 Al Snow vs. Big Boss Man – Kennel From Hell Match

It's hard to tell what was worse: this

match

concept, the match itself, or the commentators trying DESPERATELY to make this into something other than a complete farce

To quote Mick Foley, ‘ladies and gentlemen, what you’re about to witness…is truly hideous’.

The Kennel From Hell match was a nightmarish match stipulation that featured two wrestlers inside a wrestling ring, which was located inside a steel cage, which was itself located inside a Hell in a Cell.

Between the cage and the cell were what WWE commentators tried to describe as ‘vicious dogs’ that would attack anyone that tried to leave. But these dogs spent less time barking or looking scary and more time humping each other and defecating around the ring (the latter being symbolic of this match itself).

The match was a disjointed mess, with various ridiculous weapons being used as well (including, of all things, a snow shovel). Al Snow & Boss Man kept hitting each other with various objects while the commentators were either laughing (Jerry Lawler) or spewing utter nonsense (Kevin Kelly).

The only redeeming moment in this contest came when Al Snow pulled out Head, and everyone got to make countless ‘head’ jokes for the next five minutes.

This match was awful and is only worth watching for historic purposes. It was voted the Wrestling Observer’s Worst Match of the Year, and was thankfully the first and last iteration of this ridiculous concept.

#1 The Bushwackers vs. The Iron Sheik & Nikolai Volkoff – Heroes of Wrestling

Part 1:

Part 2:

‘Heroes of Wrestling’ is widely regarded as THE worst wrestling show of all time. Even if WWE were to somehow create a match featuring Roman Reigns wrestling himself, it would still be better than H.O.W.

The show was composed of matches featuring wrestlers long past their primes, including a main event between four wrestlers with a combined age of over 200. While WWE did that too at their Crown Jewel event, that match was a 5-star spectacle compared to this utter garbage.

Everything about this match was bad: the offense, the pacing, the selling, the presentation, the commentary, everything. It was abysmal, an affront to pro wrestling if there ever was one. The fans even chanted ‘USA, USA’ for this match, despite none of the four men being American.

As further testament to just how bad this eight-minute trash heap was, it received absolutely scathing reviews. Dave Meltzer initially rated it ‘absolute zero’ (i.e. zero degrees Kelvin which is about, -459.67 degrees Fahrenheit), before eventually settling on a still-awful MINUS FIVE STARS.

Meanwhile, Bryan Alvarez of Figure Four Weekly gave it “minus more stars than there are in the universe, and the universe is infinite.” If that won’t tell you how bad this was, I don’t know what will.