Most Memorable Matches and Moments In SummerSlam History

It has long been hailed as the biggest party of the Summer and one of WWE’s core 4 PPV events on an annual basis. 

Today, we re-relive the greatest matches and moments from this historic event. 

But first, let’s go over some SummerSlam facts:

  • The inaugural SummerSlam event was held in 1988 and headlined by the Mega Powers (Consisting of Hulk Hogan and Randy Savage) taking on the MegaBucks (Ted DiBiase and Andre The Giant)

  • This event was the birthplace of the TLC match (Back in 2000)

  • Undertaker has competed in the most SummerSlam events

  • Bret Hart can thank SummerSlam for his triple-crown status. He became a triple-crown champion winning the tag-team title, IC title and World Championship at separate Summerslam events 

So, let’s go through some of the best matches and moments in the history of SummerSlam in chronological order. 

SummerSlam 1988

From SummerSlam 1988, the Ultimate Warrior defeated the Honky Tonk Man to become the new Intercontinental Champion. 

If you recall, this was originally supposed to be Brutus Beefcake until he was taken out by Ron Bass. Honky did not want to be informed of his replacement and it clearly backfired. 

Also from the same event, Hulk Hogan and Randy Savage defeated MegaBucks (Ted DiBiase and Andre The Giant)

In one of the bigger what-if situations in WWF history, it was originally scheduled to be Ric Flair vs Macho Man for the WWF Championship, but negotiations with Flair fell through and he remained with NWA.

In the most memorable moment of the match, Elizabeth distracted special guest referee Jesse the Body Ventura by ripping off her skirt and exposing her red panties. No yellow polka dot bikini as promised, but male fans were still sent home happy. 

SummerSlam 1989

This was by no means a great card, but perhaps most memorable was the Ultimate Warrior defeating Rick Rude for the Intercontinental Championship 

SummerSlam 89 also featured the bizarre main event of Hulk Hogan and Brutus the Barber Beefcake vs Zeus and Macho Man.

SummerSlam 1990 

One of my personal favourite moments was the Texas Tornado, Kerry Von Erich defeating Mr. Perfect for the Intercontinental Championship. Go back and watch the incredible sell from Mr. Perfect after that discuss punch.

The Hart Foundation defeated Demolition in Two-out-of-three falls match for the WWF Tag Team Championship. This was undoubtedly Demolition’s best match as a team and the final reign for the Hart Foundation.

SummerSlam 1991 

Many memorable moments took place here

  • Macho Man and Miss Elizabeth got Married

  • Bret Hart defeated Mr. Perfect for the Intercontinental Championship in my all-time favourite match between the two. In reality, Mr. Perfect was suffering from a back injury but cared enough about putting Bret over to go out and put on an instant classic. 

  • The Legion of Doom (Animal and Hawk) defeated The Nasty Boys in a Street Fight to capture the WWF Tag-Team Championship 

SummerSlam 1992 from Wembley Stadium in London, England. 

It’s often forgotten that fans in the US were forced to wait 2 days for the event to air. 

The original location for SummerSlam 1992 was supposed to be at the Capital Centre just outside of Washington DC, but with European tours generating excellent revenue, Vince went with plan B, and we’re all grateful for that decision. The event made just shy of 3 million at the gate, which was massive business in the early 90s.

In one of the greatest main events in SummerSlam history, The British Bulldog defeated Bret Hart to capture the Intercontinental Championship in front of 80,000 fellow countrymen. 

Despite coming up short, Bret’s stock skyrocketed and this was essentially a proof of concept for a future World Heavyweight Championship run, which occurred just a few months later in October against Ric Flair in Saskatoon.

I’m going to skip over SummerSlam 1993 and focus on SummerSlam 1994

There were two very memorable moments from this event. 

For better or worse, it was the Undertaker vs the Fake Undertaker. If you recall, actor Leslie Nelson was even brought in to solve the mystery. 

More importantly, this event featured, in my humble opinion, the greatest steel cage match of all time between Bret Hart and Owen over the WWF World Heavyweight Championship. 

SummerSlam 1995 was arguably one of the worst in history, but it did feature the ladder rematch between Shawn Michaels and Razor Ramon.

I vividly recall renting this tape from the video store multiple times and skipping over nearly the entire card and just re-watching this match about a dozen times. 

SummerSlam 1996 

Mankind vs Undertaker competed in the very unique and still much-discussed Boiler Room match. Paul Bearer ultimately turned on The Undertaker by slamming him in the head with the urn, to align himself Mankind. 

Shawn Michaels ended up retaining over Vader in what many considered to be an upset. At the time Vader was positioning as an unstoppable monster. 

SummerSlam 1997 

This event featured my all-time favourite poster with Bret Hart standing in the front and the Undertaker behind him within the dark clouds. Very effective. 

The show opened with a very underappreciated steel-cage match between Mankind and Triple H.

Memorable for all the worst reasons, Owen Hart ended up dropping Stone Cold Steve Austin on his neck after a botched piledriver. Austin was temporarily paralyzed from this. 

Speaking of underappreciated matches, the main event featuring Bret Hart vs The Undertaker for the WWF World Heavyweight Championship with Shawn Michaels as the guest referee was fantastic. Up until this point, it was undoubtedly Taker’s best match.  

Shawn went to hit Bret with a chair, but he ducked and struck Taker instead. This allowed Bret to win the WWF World Heavyweight Championship 

SummerSlam 1998 

Triple H defeated the Rock at a ladder match for the Intercontinental Championship at MSG. This was a real breakthrough moment for Triple H that proved he could be a top star for years to come. As for the Rock, he was already on his historic rise to stardom. 

SummerSlam 1999 

One of only two SummerSlam events where all three major titles changed hands. 

Not the strongest card, but known for Mankind defeating Stone Cold Steve Austin and Triple H to capture the WWF World Heavyweight Championship. 

SummerSlam 2000 is best known as the birthplace of the TLC match. 

This match between the Dudley’s, the Hardy’s along with Edge and Christian changed the course of history. 

It also featured some well-known spots such as Jeff’s failed Swanton Bomb through the table, Bubba being knocked to the outside through for-double-stacked tables along with Matt suffering the same fate as well. 

Steve Blackman also knocked Shane McMahon high up off the set which led to Shane following 40 Feet onto the concrete floor. 

SummerSlam 2001 transpired in the middle of the Invasion angle. 

  • Kurt Angle defeated Stone Cold Steve Austin to become the new WWF World
    Heavyweight Champion 

  • The Rock defeated Booker T to capture the WCW Championship aka Big Gold 


Summerslam 2002 was really the beginning of the initial short-lived Brock Lesnar era as he defeated the Rock for the WWE Undisputed Championship. 

What’s interesting is that despite the fact that Brock was a heel, the crowd was firmly behind him as they wanted the title change. 

At the time, Brock was the youngest world champion in WWE history at 25 years old.

But the most memorable moment of the event was a hellacious Street fight between Shawn Michaels and Triple H where they beat the holy hell out of each other. This was Shawn’s in-ring return after a 4-year hiatus which lead arguably an even more memorable run than his original one. 

At SummerSlam 2003, Triple H defeated Goldberg, Chris Jericho, Kevin Nash, Randy Orton and Shawn Michaels to retain the World Heavyweight Championship. 

One of the most memorable spots of the match transpired when Goldberg speared Chris Jericho through the pod. 

At SummerSlam 2004 which took place in Toronto, Randy Orton became the youngest World Heavyweight Champion at 24 years old when he reversed the Crippler Crossface attempt and landing a picture-perfect RKO on Chris Benoit. 

The next night on Raw, Orton Evolution turned on him. 

SummerSlam 2005 marked Hulk Hogan’s first appearance on the PPV since 1991. He headlined vs Shawn Michaels. 

Perhaps most memorable was the fact Hulk Hogan won the match as Shawn was younger, much more active and quite frankly, much better. It was the wrong decision. The heel turn from Shawn Michaels leading into this match was incredible too. 

I’m going to be skipping over several events here and jump to SummerSlam 2008

In what has become one of the best Hell In a Cell matches over the past 12 years, the Undertaker headlined by defeating Edge. 

SummerSlam 2009 featured several great matches including: 

  • Dolph Ziggler vs Rey Mysterio for the Intercontinental Championship 

  • Legacy vs DX 

  • CM Punk defeating Jeff Hardy in a Tables, Ladders, and Chairs match for the World Heavyweight Championship

SummerSlam 2010 featured a memorable moment as opposed to a memorable match when it was Team WWE vs Team Nexus in a 7 on 7 tag-match. It did feature the return of Daniel Bryan to the promotion as well. 

SummerSlam 2011 had two major title changes transpire. 

Randy Orton defeated Christian No Holds Barred match to become the new World Heavyweight Champion. I love the chemistry between those two.

CM Punk (c) defeated John Cena (c) Singles match for the Undisputed WWE Championship with Triple H as special guest referee

Kevin Nash then returned to Jackknife Powerbomb CM Punk, which led to Alberto Del Rio cashing in his MITB contract to defeat Punk and become the new WWE Champion. 

We skip ahead to SummerSlam 2013 that featured two of my favourite SummerSlam matches. 

The first was Brock Lesnar defeating CM Punk. At this point, Paul Heyman had turned on Punk to re-align with Brock. 

Daniel Bryan also defeated John Cena to capture the WWE Championship, but the celebration didn’t last long as Triple H landed the pedigree onto Bryan which allowed Randy Orton to cash-in his MITB contract and become the new champion. 

They further established Daniel Bryan as the underdog we wanted to see on top after continually being held down. 

SummerSlam 2014 Lesnar took John Cena to Suplex City  

Lesnar proceeded to dismantle John Cena in a one-sided beatdown that lasted over 15 minutes and saw the Beast land a remarkable 16 German Suplexes 

Lesnar became the new WWE World Heavyweight Champion. A reign that lasted until Wrestlemania 31.

SummerSlam 2015 is best well known for two matches that each featured disappointing conclusions. 

The first was the long-anticipated rematch between Brock Lesnar and the Undertaker 

The second was a Winner Takes All match for WWE World Heavyweight and the WWE United States Championships between Seth Rollins and John Cena. 

Former Daily Show host John Stewart turned on John Cena by hitting him in the gut with a chair, which allowed Rollins to capitalize and hold both titles. 

SummerSlam 2016 is best known for a show-stealing match and an all too realistic moment 

The match between AJ Styles and John Cena ultimately stole the show. The match featured excellent nearfalls with both men taking each other to the limit. Styles won with Phenomenal Forearm after surviving a Super Attitude Adjustment.  

During the conclusion of Brock Lesnar vs Randy Orton, the Beast started throwing stiff elbows onto Orton with one eventually causing a giant gash onto the left side of his head. This lead to Orton bleeding like a faucet and the match being waved off and deemed a TKO victory for Lesnar. 

Rumour has it, Chris Jericho confronts Brock backstage for taking liberties and potentially injuring Orton, but apparently, that was the plan all along. 


At SummerSlam 2017, Dean Ambrose became the first Grand Slam Champion from the Shield when he captured the Raw Tag-Team Championship alongside Seth Rollins. 

SummerSlam 2018 featured several significant title changes and the beginning of ‘The Man’ as we know it 

Charlotte Flair inserted herself into the triple-threat championship match against Becky and Carmella. She ultimately won the match, which ended Carmella’s reign. 

Following her victory, Becky Lynch slapped Charlotte in the fact and proceeded to attack her. While she was supposed to turn heel in the process, the fans were adamantly behind Becky Lynch. 

Ronda Rousey put forth a dominant performance forcing Alexa Bliss to tap out to the Armbar. She became the first woman to hold WWE and UFC gold. 

And in the main event, Roman Reigns FINALLY defeated Brock Lesnar thus ending his 504-day title reign. 

With SummerSlam 2019 card being a solid one and featuring the likes of: 

  • Brock Lesnar vs Seth Rollins

  • Bray Wyatt vs Finn Balor 

  • AJ Styles vs Ricochet

  • Ember Moon vs Bayley 

  • Kofi Kingston vs Randy Orton 

  • PLUS many more!

I’m sure we will witness many more memorable moments and matches in just a few weeks.