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Seth Rollins (6-2)
Over the active short timespan of his career, Seth Rollins has already produced some incredible moments at SummerSlam to get into this list. His singles career witnessed a major boost after scoring a win in a Lumberjack Match against Dean Ambrose in 2014.
A year later, the then-Architect outsmarted John Cena in a Winner Takes All match to not only retain his WWE Championship but also win his first United States Championship and thereby become a dual champion.
The very next year, Rollins gifted one of the top match contenders for the year against the newly debutant on the main roster, Finn Balor but he came up short in that inaugural Universal Championship match.
For the next three years, The Visionary of Drip walked out of SummerSlam with Raw Tag Team Championship, the Intercontinental Championship, and the Universal Championship, respectively. In 2019, he pinned Brock Lesner to win the Universal Title at both WrestleMania and SummerSlam which is an incredible record.
His last two SummerSlam matches with Dominik Mysterio and Edge didn't have any championship gold on the line but that didn't stop him from delivering the best matches on the card. Rollins is still a top superstar on Raw and he is expected to produce more such gems down the road.
Triple H (8-5)
Over the span of 17 years between 1995 and 2012, Triple H competed in thirteen matches and won eight of those to cement himself as one of the marquee players at SummerSlam.
After a debut win over Bob Holly, he went on to have a hellacious Steel Cage match against Mankind in 1997 followed by an iconic ladder match against The Rock over the Intercontinental Championship, the very next year.
In the 2002 edition, an Unsanctioned Street Fight gave birth to the best match of the feud between Triple H and Shawn Michaels. 2003's Elimination Chamber main event match win over the World Heavyweight Championship is also one of the most-talked matches in SummerSlam history.
Triple H went on to pick up wins over Eugene, The Great Khali, Legacy faction, King Booker, and The McMahons over the course of the next few years while in his last SummerSlam appearance he put over Brock Lesnar on the latter's way to become The Conqueror.
Randy Orton (8-7-1)
Since his debut in 2002, Randy Orton is one of the most familiar names to have performed in The Biggest Event of the Summer with eight wins, seven losses, and one match that ended via TKO.
Orton's first big win of his career occurred in 2004 when he knocked off Chris Benoit to become the youngest world heavyweight champion in WWE history. The process of building a Legend Killer in him continued as took on The Undertaker, Hulk Hogan, and John Cena in the next few years.
In 2011, Orton culminated in his stretched rivalry with Christian by clinching a No Holds Barred win over the World Heavyweight Championship. After a year's hiatus, he cashed in his Money in the Bank contract to pin Daniel Bryan and win the WWE Championship, creating one of the most shocking moments in WWE history.
The following year, The Apex Predator put over Roman Reigns in a memorable outing. For the rest of the 2010s, he squared off against Sheamus, Brock Lesnar, Rusev, and Kofi Kingston in not-so-memorable matches.
However, the future WWE Hall of Famer bounced back in 2020 by participating in a solid physical WWE Championship match against Drew McIntyre. Also last year, his Raw Tag Team Championship with Riddle received one of the loudest pops in SummerSlam history.
Edge (12-2)
Despite his incredible track record, Edge's name remains underrated when it comes to SummerSlam history. But statistics show that the Hall of Famer has lost only two matches at the summer spectacle.
One of those losses came in a Tag Team Turmoil match, all the way back in 1999 while the other loss occurred against The Undertaker inside Hell in a Cell in 2008. Both these bouts are top-notches to have upped his game.
The first-ever official Tables, Ladders, and Chairs Match for the Tag Team Titles had Edge team up with Christian against The Hardy Boyz and The Dudley Boyz. The three legendary tandems put up an instant classic, forcing WWE to arrange more TLC matches, down the road.
In 2005, The Rated-R Superstar solidified his moniker and rose to stardom as a singles competitor by obliterating Matt Hardy in a highly personal contest. Next year, Edge defeated John Cena in the latter's home-state for the WWE Championship in one of the biggest wins of his career.
After missing SummerSlam in 2007 and 2009, the eleven-time world champion played a part in Nexus' downgrade on the roster before heading into unexpected retirement. After the monumental comeback, Edge delivered the best match of the SummerSlam 2021 card against Seth Rollins, living up to his standard.
Brock Lesnar (6-4)
No superstar has been more dominant than Brock Lesnar in the history of SummerSlam even after considering the four losses he had experienced.
Back in 2002, Lesnar decimated The Rock to become the youngest WWE Champion, at that point, emphatically declaring that 'the next big thing' has arrived in the WWE. He lost the title a year later to Kurt Angle at SummerSlam 2003 before he eventually left the WWE.
A decade later, The Beast Incarnate was again unleashed on the WWE Universe who went on to not only clinch a win over Triple H at SummerSlam but also break his arms for good.
Lesnar's hot streak at the summer pay-per-view continued as he bested CM Punk in 2013 and then John Cena, the very next year. Suplex City turned into a reality during the bout against Cena and history shows no other superstar showed such dominance over WWE's franchise player in a WWE Title match.
The Undertaker managed to secure a win over Lesnar in 2015 but he never pinned or submitted him. In 2016, Lesnar returned to the winning track, by picking up a TKO win over Orton in a match filled with blood.
The then-longest Universal Championship reign continued for the top-most superstar of the WWE as he toppled three elite Raw Superstars in a Fatal-4-Way SummerSlam Main Event.
2018 and 2019 installments brought back-to-back losses for him from Roman Reigns and Seth Rollins, respectively with the Universal Title hanging in the balance.
The quest of getting that title back continued for Lesnar when he made a triumphant return at last year's SummerSlam to confront Roman Reigns. This Sunday, the eight-year-long saga will finally come to an end when the duo will collide in a Last Man Standing Match for the Undisputed WWE Universal Championship.
