5 Best Wrestling Matches of 1999

Depending on who you were, 1999 was either one of the best years in wrestling or one of the worst. For those who enjoyed their wrestling as traditional grappling, it wasn’t that great of a year outside of AJPW.

WWE was turning into more of a ‘crash-TV’ style show, with more chaotic matches centered on hardcore violence and soap-opera storylines than chain-grappling. Don’t get me wrong, some of the best wrestling stories ever happened during 1999, but those stories meant that actual wrestling was replaced with interference, belt shots and screwjobs left and right.

WCW wasn’t doing much better, as internal politics and failing numbers caused some bad storylines to emerge. The good matches in WCW were few and far between, with only one of them being good enough to make this list.

Even New Japan Pro Wrestling, once a hub of spectacular wrestling, started to falter as then-owner Antonio Inoki fell in love with MMA. That MMA-centric focus would cripple his company so badly that NJPW wouldn’t rebound as a company until ten years later.

The only company that seemed to be unaffected by the world going crazy was All Japan Pro Wrestling, which remained the same MOTY factory as it had been for the past decade. However, problems were looming for them as well. AJPW owner and booker Giant Baba died in 1999 and the company’s future was in doubt.

Worse, the wrestling style of King’s Road peaked in 1999, which meant that it was much harder, if not impossible, for any future matches to ever captivate the audience as did the matches of yesteryear.

So which matches in 1999 have been immortalized as the year’s best? Read on…

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5. Bret Hart vs. Chris Benoit – October 4, 1999

This match was one of the most emotional matches ever televised. It took place on a tribute show dedicated to Owen Hart, so things were a bit somber, to say the least. That said, this was an awesome grappling contest with a very deep underlying story.

You had two outstanding natural grapplers that had been trained by Hart Family patriarch Stu Hart wrestling a pure wrestling match dedicated to the memory of Bret’s brother Owen.

As a pure grappling contest, this was a great match. The action was crisp and clean, the transitions and reversals were executed perfectly (pun intended), and the crowd was hypnotized by the wrestling going on. This is made even more amazing by the fact that Bret was very much winding down by this point, and would be forced into retirement within the next year or so.

It was very touching sight to see both Bret and Benoit motion to the heavens to Owen, and for the crowd to acknowledge the important role Owen Hart played for many people. You couldn’t ask for a more ideal tribute to one of the best grapplers in Owen Hart than to have two of the best in-ring workers of the 1990s to put on such an impressive technical wrestling match.

4. Stone Cold Steve Austin vs. The Rock – Ho Holds Barred – Backlash 1999

In another perfect example of ‘Steve Austin versus everybody’ booking that made WWE so white hot in 1999, Austin faced his arch rival the Rock for the world title. But there the added caveat that if he so much as touched Shane McMahon – who was appointed special guest referee for this match – he’d lost the title. It was a great stipulation that made the drama in this match much more palpable.

This was a fast-paced, white-hot brawl with a raucous crowd that loved the match from the moment it started. It was never meant to be a technical wrestling match, but in this case that was a good thing. The chaotic nature of this savage brawl made it so much better than if they were confined to the ring. Rock and Austin went through metal cages and got slammed onto the floor several times, which made both of them look much tougher than if they were ‘only’ slammed onto the ring canvas.

Also, this match has one of the best and funniest moments of the year. The Rock taunted a prone Austin by grabbing a camera and flipping him the bird, only for Austin to get up, flip the Rock the bird, and then hit the Stunner through the table. It was an awesome visual.

Finally, the match had one of those crazy WWE endings which involved, among other things, a corrupt referee, belt shots to the head, and Vince McMahon hitting his own son Shane. Don’t even try to understand it; just watch this match for the mindless chaos and craziness.

3. Kenta Kobashi & Jun Akiyama vs. Mitsuharu Misawa & Yoshinari Ogawa – October 23, 1999

A lot of people have wondered why Wrestling Observer’s Dave Meltzer had such high praise for AJPW during the 1990s. I believe I’ve found the main reason: AJPW matches were pure grappling contests with few gimmicks and emphasis on drama based on big moves and toughness.

This match exemplified those traits. You had two teams, one composed of tag team champions and the other of challengers. The wrestlers involved didn’t have over-the-top gimmicks; all of them were straightforward grapplers who used elaborate wrestling moves and clever reversals to try and win.

And last but not least, they used some of the craziest wrestling moves ever created, including the legendary Burning Hammer, a move so high-risk and powerful that it’s almost never used, even in Japan.

The reason this match is so good is because it has all those elements of a great match: drama, big moves, a raucous crowd, technical precision, logical reversals, unpredictability and moves so dangerous and powerful it makes you think the wrestlers are made of iron.

Without knowing anything about any of these four men, you get the feeling they’re all tough as nails and can back up that toughness with great technique as well.

It’s a really fun match that doesn’t require any translation or context.

2. The Hardyz vs. Edge & Christian – Ladder Match – No Mercy 1999

This was also the first-ever tag team ladder match, so people didn’t really know what to expect. It was also a match between two teams of young, up-and-coming stars that needed to go all out to make a name for themselves.

And boy, did they ever.

These four wrestlers put on one of the most innovative matches in WWE history. There were moves and spots that no one had ever seen before, including some of the most shocking and high-risk moves ever. The ladders were thrown around like weapons, and both teams used some terrifying ladder-centric attacks on each other.

These included: a DDT and a Suplex off the ladder, body splashes into ladders, powerbombs off ladders, a leapfrog legdrop from the top rope over a ladder, ladders being thrown around like chairs, ladders being smashed into one wrestler’s groin, people being thrown face-first into ladders, finishers off ladders, and at one point, Jeff Hardy dove onto a ladder to have the legs smash into Christian’s face.

The crowd was on fire throughout this match, and gave them a standing ovation several times. Keep in mind that none of these four men were top stars; all of them were mid card guys, yet the fans showed their appreciation several times.

In the years that followed, these teams would meet several times in ladder-based matches, which led to even more legendary matches. Though this match was relatively tame in comparison to those later matches, it was still a chaotic and exciting match that helped elevate all four wrestlers’ respective careers.

1. Kenta Kobashi vs. Mitsuharu Misawa – June 11, 1999

There are some wrestlers that can have countless matches together without it ever getting repetitive or boring. Kenta Kobashi versus Mitsuharu Misawa is one such a match-up, because they do so much that each bout feels fresh and different. Few wrestlers, if any, can do that as well as these two.

In another Match of the Year classic, Kobashi and Misawa battle for All Japan Pro Wrestling’s most prestigious prize, the Triple Crown Heavyweight Championship. And just like in the prior year’s titanic encounter, you had one of the best pure wrestling matches in the world.

These two are so good in the ring that they manage to make even the smallest moves mean something and get a reaction from the crowd. Whether it’s a simple elbow strike, a knife-edge chop to the chest, or even a headlock takedown, the audience reacts with cheers. That is the definition of crowd control, which is a skill that’s hard to teach in wrestling.

But most importantly, Kobashi and Misawa are the masters of building up big moves. In this match (as with most of their biggest encounters), they build up a big spot (like a Powerbomb or a toss of the apron) by teasing the left before the intended victim reverses out of it. From there, either the intended big move is hit or the other person hits a big move of their own. Either way, when the move it hit, the crowd goes nuts and it makes the story between them even better.

This is a must-watch for anyone that likes high-risk wrestling with big moves and no gimmicks. It’s all about wearing down your opponent with as many strong moves as possible, weakening them with smart limb targeting, and in general being as tough as possible.

In other words, this is wrestling as art and in terms of art, it’s a masterpiece, plain and simple.