The 30 Greatest Matches in WWE SummerSlam History

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SummerSlam is coming this Sunday live from Toronto, Canada and is sure to be one hell of a show. For a long time, SummerSlam has been seen as the second biggest show of the year when it comes to WWE, with WrestleMania, of course, being top dog. The “Biggest Party of the Summer” has seen its fair share of historic moments and incredible matches year in and year out. The first event occurred all the way back in 1988. All these years later in 2019, there have been plenty of classic matches in its history.

There have without a shadow of a doubt been plenty of in-ring classics that fans to this day love to go back and watch, and plenty of possible hidden gems that fans just forget. I have compiled a list that will go in chronological order taking a look at 30 of the best matches in SummerSlam history. Of course, there will be plenty of disagreement, so please add what matches you may feel deserve the spotlight to only make the list greater.

Without further ado, here are the 30 Greatest Matches in SummerSlam History (Note: This list is entirely subjective to Scott)

The Hart Foundation vs The Brain Busters (1989)

SummerSlam

SummerSlam has a rich history of tag team matches and you do not have to look further than the first match on this list. The Brain Busters, made up of Arn Anderson and Tully Blanchard with Bobby Heenan at ringside, went to battle with Bret Hart and Jim Neidhart in a non-title mat classic that kicked off SummerSlam 1989 in the hottest way possible. The Brain Busters would manage to sneak out the victory in this one.

2 out of 3 Falls: The Hart Foundation vs Demolition (1990)

When two of the best tag teams in the history of wrestling go at it, you know it is going to be an instant classic. The crowd was on their feet all match long as Demolition did all they could to try and fend off The Hart Foundation. It would be The Road Warriors who would allow referee Earl Hebner to realize Ax and Crush were pulling the switch, allowing Bret and Neidhart to capture the third fall and the victory as “The Anvil” hit the shoulder block, allowing Bret to roll him up and become the new tag team champions.

Bret Hart vs Mr. Perfect (1991)

Summerslam

Highly regarded as possibly the best match in SummerSlam’s history, Bret Hart and Mr. Perfect put on a technical masterpiece for the Intercontinental Championship in 1991. It was close fall after close fall as there was shock on both the faces of Hart and Perfect in this one. Bret would have the wherewithal to kick out of the Perfect-Plex mid match which left the crowd on their feet. The end of this stellar bout between these two legends would come when Hart would catch Perfect’s leg on a leg drop, twisting it into the Sharpshooter and becoming the new Intercontinental Champion.

Ultimate Warrior vs Randy Savage (1992)

Ultimate Warrior and “Macho Man” Randy Savage are two of the biggest icons in the history of professional wrestling and they had a classic bout at Wembley Stadium for the world championship. Mr. Perfect and Ric Flair were outside and continuously confused the commentators and performers in the ring as to what side they were on. It would finish when Warrior would win by count-out following Ric Flair smashing his knee in. The respect shown between the two to finish the match was perfect, and while there was no pin victory, it was a classic.

Bret Hart vs The British Bulldog (1992)

Summerslam

Bret Hart’s name is near synonymous with SummerSlam, as the second generation Superstar often put on some of his best matches at the summer classic. Having stolen shows in tag action with the Hart Foundation and the year previous against Mr. Perfect, Bret Hart followed up 1991’s instant classic with another one, this time in a battle of family. He feuded with his real-life brother-in-law “British Bulldog” Davey Boy Smith – with his sister and Bulldog’s wife, Diana Hart, a part of the action – culminating in a huge match at Wembley Stadium in London, England. Regarded as one of the best matches of Bulldog’s career, it was another great piece of storytelling, that united Hart and Bulldog together in a way that had never been presented before on camera, setting the groundwork for the new Hart Foundation five years later.

Shawn Michaels vs Mr. Perfect (1993)

This is one of plenty of Shawn Michaels‘ matches to make this list. There really never is enough of the Heartbreak Kid either. This time around is Shawn defending his Intercontinental Championship against Mr. Perfect. What is so great about these two is that it doesn’t have to be a 30-minute duel to finish as a classic. The experienced Perfect and the young gun Shawn was the perfect combination in 1993, with Shawn coming out with the victory via count-out with Diesel getting involved.

Steel Cage: Bret Hart vs Owen Hart (1994)

Summerslam

While Bret vs Owen had happened earlier this year – the amazing WrestleMania X opening match that saw Owen upset his World Champion level brother – it was their rematch at SummerSlam in 1994 that fully proved to the world that Owen Hart wasn’t just Bret’s little brother anymore. The heated Hart family rivalry devoured the WWF for years, and Bret and Owen’s story of strife and jealousy was one of the best angles of the New Generation. Bret would win the rematch in another Hart brothers classic, but by this time, Jim “The Anvil” Neidhart had chosen to side with Owen in the family spat and it would continue to drive a wedge in the family until they all reconciled in 1997.

Ladder Match: Shawn Michaels vs Razor Ramon (1995)

Summerslam

A WrestleMania rematch from a year earlier that was never supposed to happen in the first place. While the original may have changed the game, this rematch between Shawn Michaels and Razor Ramon was possibly even better than the original. Shawn Michaels took one hell of a beating in hopes of retaining his championship, which he would accomplish. Razor and HBK had a chemistry that proved to be undeniable, putting on a ladder classic that topped the more historic bout.

Shawn Michaels vs Vader (1995)

For Vader fans, they don’t necessarily look at this one as a bright spot. While the match was restarted two separate times, Shawn Michaels and Vader put on one of the best big men vs underdog matches in SummerSlam history. Shawn Michaels was on another level at this time, and mixing that with the crazy athleticism of Vader put together one of the more underrated championship matches in SummerSlam history. Vader was another level where HBK could prove himself.

Boiler Room Brawl: Mankind vs Undertaker (1996)

Summerslam

Maybe the most unique match on this entire list. Mankind and Undertaker‘s legendary rivalry only get stronger and stronger with these two competing in the first ever Boiler Room Brawl. Paul Bearer would turn on the Undertaker, allowing Mankind to smash Undertaker with the urn to win the match. It was wild, it was fun, and it was one of many classics between these two.

Bret Hart vs Undertaker (1997)

Summerslam

Behind the scenes, Bret and Taker were close friends, which only made their encounters on camera feel more connected. This match for the WWF World Championship was the duos finest combination, and it happened during the early stages of the Attitude Era’s developing stages. Bret used his technical savvy to keep the Undertaker grounded for the most part, but it was the involvement of special guest referee Shawn Michaels that added the final chapter of this match. He brought a chair to the ring to use against Hart, but instead hit Undertaker, costing him the match. This lead to Taker and HBK’s historic Hell In A Cell match and would launch the epic DX vs Hart Foundation feud that would dominate the year.

Ladder Match: Triple H vs The Rock (1998)

Summerslam

Many consider this as the first great match in The Rock‘s career, possibly the breakout. Triple H and Rock have a long storied rivalry that is one of the best in WWE history and this is one of their true classics. After almost a whole 25 minutes, Triple H became the new champion that night in one of the more underrated ladder matches in the companies history.

Stone Cold Steve Austin vs Undertaker (1998)

The second match from the 1998 SummerSlam is one of the most anticipated in the event’s history. Stone Cold Steve Austin defending the WWE Championship against the Undertaker in the main event right in the middle of Madison Square Garden. These men put each other through hell, fighting all-around the ring in an absolute brawl. Austin would find victory when the referee would be looking away and allowed him to hit the low blow, then a good ole Stone Cold Stunner for the finish. The respect shown between to the two at the matches end was a perfect way to end this epic clash.

TLC: Edge & Christian vs The Dudley Boyz vs The Hardy Boyz (2000)

Summerslam
Photo: WWE

The first-ever Tables, Ladders, and Chairs match occurred at SummerSlam 2000 between the three teams that innovated and opened eyes for so many current day tag teams. Edge and Christian managed to successfully defend their tag team titles against their rivals The Dudley Boyz and The Hardy Boyz, winning the first-ever match and helping set a precedent that would only be followed by these three teams once again.

Stone Cold Steve Austin vs Kurt Angle (2001)

Summerslam
Photo: WWE

Stone Cold representing the Alliance while Kurt Angle was doing all he could to bring the championship back to the WWE. Nothing better than a hot crowd, even if it was mixed throughout the match. Heel Austin will never be something acceptable, but all match long of Kurt Angle getting screwed out of victories due to Austin attacking referees and not following the rules, leading to a DQ, it allowed for an even bigger moment after SummerSlam, but these two put on a show.

Non-Sanctioned: Shawn Michaels vs Triple H (2002)

Photo: WWE

Shawn Michaels made the return no one expected after four years away, returning at SummerSlam to face Triple H in a non-sanctioned match. These two men brutalized each other in a match where Shawn Michaels show he really did still have it. It was personal, it was ruthless, and was overall one of the best matches between these two. Shawn Michaels would win his first match back when he would reverse the Pedigree into a pining combination to secure the victory. These would only lead to more legendary bouts between them, but these two went to war and helped Shawn prove he still had it.

Eddie Guerrero vs Kurt Angle (2004)

Summerslam
Photo: WWE

When you read these two names, would you really expect anything else but a classic? Eddie Guerrero and Kurt Angle went one-on-one in singles competition at SummerSlam 2004 and accordingly did not disappoint. Angle worked Eddie’s ankle all match long but the resilient Guerrero would continue to fight it off. He would have to tap out despite his vintage ways and Kurt Angle would leave victorious in another great encounter between these two men.

Shawn Michaels vs Hulk Hogan (2005)

Summerslam
Photo: WWE

A classic for all the wrong reasons possibly. First of all, Shawn Michaels vs Hulk Hogan is as big a match you could have in wrestling history. The only problem is that Hulk Hogan was only going to do one match, resulting in Shawn Michaels to go to extreme measures. Shawn was flying and flopping all-around the ring in spite of this fact, as Hulk Hogan would walk out victorious but this is one of the greatest because of how ridiculous it is.

John Cena vs Randy Orton (2007)

Summerslam
Photo: WWE

John Cena and Randy Orton. One of the most storied rivalries in WWE history. This would be the official kick off of sorts to their crazy number of matches against each other, with this being the first PPV singles match between the two men. Cena would have enough to win the first bout between the two in one of their bests. He successfully defends his WWE Championship and only being the first of many chapters in this long rivalry.

Hell in a Cell: Undertaker vs Edge (2008)

Summerslam
Photo: WWE

The Undertaker and Edge had one of the most heated rivalries of all-time that started in 2007 and really found its finish right here inside Hell in a Cell. Undertaker returned at SummerSlam to face Edge and sent him straight to hell. After a grueling match where The Undertaker even hit a Con-Chair-To on Edge, he finished him off with a Tombstone. The final image was Edge being sent through the ring, Undertaker getting on his knees and making the whole in the ring light on fire. A memorable image and a great match.

TLC: CM Punk vs Jeff Hardy (2009)

Summerslam
Photo: WWE

In 2009 there was not a more popular star than Jeff Hardy, who went into this match as World Heavyweight Champion. Hardy put it all on the line in hopes of defeating his rival CM Punk, who made it as personal as he ever could. It would be a TLC match that brought the climax of this feud. Despite never being in a TLC match in his career to this point, CM Punk had enough to capture the victory even though Hardy did all he could to try and put Punk out. One of the best stipulation matches in the history of SummerSlam.

No Holds Barred: Christian vs Randy Orton (2011)

Photo: WWE

The rivalry below may have ruled the summer of 2011, but it was Christian and Randy Orton who put together one of the most underrated feuds in recent history. After trading the World Heavyweight Championship back and forth for much of the summer, it would culminate at SummerSlam in one of Randy Orton’s best career matches. The chemistry these two men is overlooked by many but one of the best feuds and matches in the past decade. The phenomenal ending to the phenomenal bout was when Randy Orton caught Christian with an RKO as Christian went for a springboard and was met with the RKO on the steel steps.

John Cena vs CM Punk (2011)

Photo: WWE

Two WWE Champions battled in one bout to become the undisputed, true WWE Champion of the company. It was John Cena facing what was possibly his greatest rival in CM Punk just a month after their all-time classic at Money in the Bank. John Cena never had better chemistry with another wrestler more than he had with CM Punk. With Triple H as the special guest referee, there was guaranteed to be a winner and one WWE Champion promised Triple H. It was the second “Summer of Punk” in 2011, from his Pipebomb to him leaving with the WWE Championship, to this where he once again defeated John Cena to be the only champion. While he was unfortunately cashed in on after the match, this was far and away the year of the “Straight Edge Savior” and another classic by these two top guys.  Full match is available for FREE on WWE’s youtube channel.

No Disqualification: CM Punk vs Brock Lesnar (2013)

Photo: WWE

“The Best vs The Beast”. A program stemming from CM Punk’s days as a “Paul Heyman Guy”. CM Punk became obsessed with trying to get back at Paul Heyman for betraying their friendship and siding with Brock Lesnar. This would lead to “The Best in the World” facing “The Beast Incarnate” in the ultimate David vs Goliath match. Still possibly the best match of Brock Lesnar’s second run with the WWE, these two men put each other through the wringer to win this match. CM Punk had the crowd on their feet a number of times, including towards the end when he hit a GTS but proved to not be enough. Punk’s obsession with getting a hold of Paul Heyman is what would leave him on the mat for the three count and the loser in this bout. An F5 from Brock to win the match was the ending we expected, but the match was not. Punk got every ounce of effort out of Brock Lesnar in this one and is Punk’s last memorable match of his career. A SummerSlam spectacular in terms of match quality.

John Cena vs Daniel Bryan (2013)

Summerslam
Photo: WWE

The “YES” was alive and well in 2013 when John Cena selected Daniel Bryan as his challenger for the WWE Championship at SummerSlam. And an instant classic it would become as Daniel Bryan accomplished something no one ever thought would be possible. He not only pinned John Cena clean in the middle of the ring but became the WWE Champion and displayed a moment all fans wanted, even if short-lived.

John Cena vs Brock Lesnar (2014)

Summerslam
Photo: WWE

Destruction. Devastation. Complete, utter shock. Brock Lesnar had the biggest year of his career in 2014 and that only continued at SummerSlam. John Cena went in as the WWE World Heavyweight Champion and left as a shell of himself. This is where Suplex City was born as Lesnar destroyed John Cena on his way to becoming the new world champion and showing a new side of domination no one expected. A match that will never be forgotten.  Also available for free courtesy of WWE’s YouTube.

Kevin Owens vs Cesaro (2015)

Summerslam
Photo: WWE

Just one night after performing at NXT Takeover: Brooklyn, Kevin Owens took on Cesaro in one of the better singles matches at SummerSlam in recent years. Having two talents like Cesaro and KO in the same ring is almost a guarantee of greatness, it’s just a matter of giving them the time to do so. KO was still fresh to the WWE Universe then but continued to put himself on the map with this incredible win over Cesaro via Pop-Up Powerbomb.  A bit of a hidden gem that WWE uploaded to their YouTube channel just days ago.

John Cena vs Seth Rollins (2015)

Photo: WWE

Despite the unsatisfying finish to this match, John Cena and Seth Rollins put on a show when both the WWE Championship and the United States Championship were on the line. This is just one of many great matches for Cena at SummerSlam, but this one was unique as Seth Rollins got the huge victory on John Cena, despite Jon Stewart being involved and helping Rollins win. One of the best matches in SummerSlam’s recent history.

John Cena vs AJ Styles (2016)

Summerslam
Photo: WWE

Who would have thought this match could ever happen? This was actually the second, but possibly the biggest between both John Cena and AJ Styles. The biggest star of the 2000s in the WWE vs the biggest star of the 2000s in TNA. Cena has put on some of the best SummerSlam bouts of all-time and this was in no way any different. Styles shocked the world and the crowd erupted when he pinned John Cena, clean, right in the middle of the ring. Possibly their best out of their trio of singles matches.  John Cena’s streak of full, free matches continues here.

Brock Lesnar vs Braun Strowman vs Samoa Joe vs Roman Reigns  (2017)

Summerslam
Photo: WWE

The only multi-man match to make it onto this list that is not a tag team match. This one between the four “juggernauts” of 2017 saw Brock Lesnar defend his Universal Championship in one of the most physical Fatal 4-Ways ever. Braun Strowman went into this match as an unproven beast and left the match an unstoppable star.  There were barricades broken, announce tables destroyed, and complete, utter disaster accomplished. Roman Reigns was still being booed out of the building but only added to his resume with this one. And for Samoa Joe, he showed he can easily hang with the biggest and the baddest. Lesnar just survived in this one as this is the most recent classic of SummerSlam.

Stay tuned to the Last Word on Pro Wrestling for more on this and other stories from around the world of wrestling, as they develop. You can always count on LWOPW to be on top of the major news in the wrestling world, as well as to provide you with analysis, previews, videos, interviews, and editorials on the wrestling world.  Where possible we have posted highlights/ the full match but we recommend you subscribe to the WWE Network to see every match.

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