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5 Best Wrestling Matches of 1999

Top 5 / Top 10

1999 was a critical and commercial success for WWE, but these two wrestlers weren
1999 was a critical and commercial success for WWE, but Rock and Austin weren't the only ones to have epic matches...

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…

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.

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