WWE Summerslam 1999 Matches Ranked From Worst To Best

Summerslam 2021 is almost here, the second biggest show of the show behind WrestleMania. Over the years we’ve seen some of the best PPVs in WWE history, and today we’re taking a look back at one of the hottest shows of the Attitude Era, Summerslam 1999. Here is every Summerslam 1999 match ranked from worst to best.

9. Ivory  vs Tori – Women’s Championship Match

From the 90s until the mid-2010s, women’s matches rarely got the time and attention they deserved, often relegated to quick matches to bridge the gap between more important feuds. Sadly this was the case with this match too, despite the talent that both possessed, primarily Ivory though, the match only got four minutes and was over before any meaningful story was told.

8. Big Boss Man vs Al Snow

Throughout the second half of 1999, the Big Boss Man and Al Snow engaged in many Hardcore Matches, including a rather dreadful Kennel From Hell match the following month. Thankfully this match was better than what was to come, with the two brawling on the streets of Minneapolis. It was fun, but rarely were Hardcore Matches anything to write home about.

7.  Tag Team Turmoil Match To Determine The Number 1 Contenders

Tag team wrestling has always been a black sheep in WWE, with the company going through phases of being all in with it, and other times it being an afterthought. Thankfully, during the Attitude Era, the WWE put more emphasis on tag team wrestling and it paid off with many legendary matches including the TLC classics. At Summerslam 1999 we saw six teams fight over the opportunity to challenge for the titles. Throughout the match it looked like Edge and Christian were set to win the opportunity, defeating three out of their five opponents. But then The Acolytes hit the ring and the two powerhouses destroyed everyone in their sight to win the match.

6. Ken Shamrock vs Steve Blackman – Lion’s Den Match

At the previous Summerslam event, we saw the first-ever Lion’s Den match, WWE’s take on MMA which saw the competitors take part in a scripted MMA-style fight. With Steve Blackman being a martial artist with a focus on using weapons, and Ken Shamrock being a former UFC competitor, the match seemed like a logical choice and overall the match was really fun to watch. We would only get to see a few of these throughout the Attitude Era, but this was certainly the highlight of them.

5. D’Lo Brown vs Jeff Jarrett – WWF Intercontinental and European Championship Match

D’Lo Brown is one of the most underrated Superstars of the era, capable of putting on solid matches with whoever he stepped in the ring with. At Summerslam 1999 both the Intercontinental and European Championships were on the line in the same match, with Jarrett scoring the win. It was a great opener and it is a shame that stars such as D’Lo Brown often found themselves in that position, but what a way to start a show.

4. The Rock vs Billy Gunn – Kiss My A** Match

While the match itself was good, it was a match designed to fail. Billy Gunn had won the King Of The Ring two months prior and it seemed that Billy Gunn would finally get his shot at the big time, with him being positioned to chase the WWF Championship. Unfortunately, that wasn’t the case. Instead, he was pushed into a feud with The Rock, and while that sounds like a dream come true, it didn’t play out that way for one half of the New Age Outlaws. During an episode of Monday Night Raw, The Rock delivered a promo that immediately killed any momentum that Gunn had, which then was followed by two PPV matches that The Rock won, including their Summerslam match which ended any potential Billy Gunn had. The match itself was really good and had Gunn won we could have seen another main event star to be included in the mix.

3. X-Pac and Kane vs The Unholy Alliance – WWF Tag Team Championship Match

X-Pac and Kane were almost the perfect tag team, with X-Pac being the high-flying member that can take punishment and sell for their opponents, while Kane is the monster powerhouse that can come and make the save. At Summerslam 1999 the pair faced off against the unlikely team of Kane’s brother The Undertaker and Big Show. The match itself was a bit clunky, with Big Show being rough around the edges, and there being three big men in the same match. But overall it was a good match, it is always fun to see X-Pac and Kane team up, and The Undertaker and Kane had incredible natural chemistry.

2. Test vs Shane McMahon – Greenwich Street Fight

Perhaps the most surprising match of the match, Test faced off against his future brother-in-law in a Greenwich Street Fight. While Test wasn’t the greatest wrestler of all time, it was a fun match that was much better than the Hardcore Match earlier in the night. Despite not being a traditional wrestler, Shane McMahon always goes above and beyond in every match he takes part in. A billionaire’s son doesn’t need to put his body on the line as Shane does, but that shows his passion for what he does and this match was a shining example of that.

1. Stone Cold Steve Austin vs Triple H vs Mankind

The main event of Summerslam 1999 was certainly the highlight of the night, with Stone Cold Steve Austin defending his WWF Championship against Triple H and Mankind with Jesse “The Body” Ventura serving as the special guest referee for the match. As expected, the three wrestling icons put on a classic match. While Triple Threat Matches can be awkward and clunky, the three Superstars managed to put on a great match. Mick Foley won the match, serving as his final WWF Championship win. He dropped the title the next night on Raw, with the rumour being that Austin didn’t want to lose the title to Triple H as he felt that he wasn’t ready, so instead chose to lose to Mankind, although this has never been confirmed.


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