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Gossip Burst Report

5 Best SummerSlam Matches (& 5 Worst)

Author

Robert Clark

Published Mar 28, 2026

Triple H has been a mainstay in the WWE for over two decades. The 14-time World Champion is one of the greatest wrestlers to lace up a pair of boots. Triple H has shone through at many showpiece events during his time in the WWE. The Game has a good track record at SummerSlam. He has elevated a few talents to the next level with his bouts at SummerSlam.

RELATED: 10 Wrestlers Triple H Needs To Face Before He Retires

There are some underrated classics, which will stand in the test of time. However, there are some which a few fans will not want to watch back again. Find out Triple H's best and worst matches at the Biggest Party Of The Summer, SummerSlam.

10 Best: D-Generation X Vs Legacy (SummerSlam 2009)

Triple H was in the midst of an ongoing personal rivalry with Randy Orton in 2009. Orton attacked Triple H's wife Stephanie McMahon before WrestleMania. Cody Rhodes and Ted DiBiase were under the tutelage of Orton in the faction Legacy. DX was reunited once more.

They arrived at SummerSlam on a tank, throwing it back to their Attitude Era days. Rhodes almost earned Legacy a shock victory with Cross Rhodes to HBK. The Game made the save for his team. Michaels nailed Rhodes with Sweet Chin music out of nowhere, bringing a halt to this entertaining contest with DX's arms raised aloft.

9 Worst: Triple H Vs Shawn Michaels Vs Goldberg Vs Randy Orton Vs Chris Jericho Vs Kevin Nash (SummerSlam 2003)

The main event of SummerSlam 2003 featured the second-ever Elimination Chamber match. Triple H's World Heavyweight Championship was on the line. The defending champion was enjoying an eight-month reign as champion to that point. Unfortunately, Triple H was nursing a groin injury. The leader of Evolution had Randy Orton in his corner as back up as Goldberg was a legitimate threat to the title.

RELATED: Every Version of Triple H, Ranked From Worst To Best

Goldberg eliminated Orton, Chris Jericho, and Michaels in this match with ease. Triple H and Goldberg were the final two participants in this encounter. Triple H retained the Championship after nailing Goldberg with a sledgehammer.

8 Best: Triple H Vs Brock Lesnar (SummerSlam 2012)

2012 saw Brock Lesnar return to the WWE after an eight-year hiatus. Lesnar engaged in a rivalry with John Cena in his second stint with the company. However, after the Beast Incarnate lost to Cena at Extreme Rules, he quickly turned his attention to Triple H. The two contested the main event at SummerSlam in 2012 in a No Disqualification match. Lesnar heavily focused on The Game's arm, which he broke a few months prior.

The two would battle back and forth and Triple H kicked out of Lesnar's F5. In the closing stages of this brutal encounter, Triple H nailed a Pedigree. Lesnar used his ring awareness, forcing the Game to submit with a Kimura Lock.

7 Worst: D-Generation X Vs The McMahons (SummerSlam 2006)

SummerSlam 2006 saw Shawn Michaels continuing his feud with Mr. McMahon and his son Shane. Michaels reunited with Triple H to reform D-Generation X and even up the odds. DX had the crowd behind them as the McMahons tried to gain the upper hand on DX. The McMahons had another trick up their sleeves, sending Finlay, Mr. Kennedy, William Regal, and Big Show to the ring to interfere on their behalf.

Before the match began, reigning ECW Champion Big Show chokeslammed Triple H through the announce table. The Game recovered, and Michaels performed his Sweet Chin Music on Vince. Triple H scored the victory after a Pedigree on Vince. It was a lackluster affair with some bright moments.

6 Best: Triple H Vs The Rock Vs Kurt Angle (SummerSlam 2000)

The main event of SummerSlam 2000 saw Triple H and Kurt Angle challenge The Rock for the WWE Championship. Angle and Triple H featured in a love triangle with Stephanie in the mix. Triple H and Angle brawled at ringside before The Rock could make his way to the ring. Angle suffered a concussion in this match following a Pedigree through the announce table.

Angle was out of the equation and taken backstage by the EMTs. It left The Rock and Triple H to battle it out one-on-one for the championship. The Olympic Gold Medalist returned to the ring, costing The Game the match. It was an instant classic.

5 Worst: Triple H Vs King Booker (SummerSlam 2007)

SummerSlam 2007 saw the return of Triple H after injuring his right quadriceps at New Year's Revolution back in January. The Game's first match in seven months was against King Booker. This encounter between the two former World Champions was not a memorable one.

The match was worked at a slow methodical pace. Booker being a solid worker was the ideal opponent for Triple H. The King of Kings dominated this bout and earned a pinfall victory with a Pedigree to the delight of the crowd.

4 Best: Triple H Vs The Rock (SummerSlam 1998)

Triple H and The Rock were on their way to superstardom in 1998. The two were the respective leaders of their factions, D-Generation X and the Nation, respectively. Triple H challenged The Rock for his Intercontinental Championship in a Ladder match.

Both combatants used the ladder to their advantage. Despite interference from Mark Henry who threw flour in Triple H's eyes, The Game claimed his second Intercontinental Championship. Chyna had a huge assist, hitting The Rock low and sending him crashing off the ladder.

3 Worst: Triple H Vs Bob Holly (SummerSlam 1995)

Before Triple H was a degenerate, he was the Greenwich Blueblood. SummerSlam 1995 was the sight of Triple H's pay-per-view debut as he squared off against Bob Holly.

The bout was a lackluster affair. Both had some bright spells, but the crowd was far from impressed. Thankfully for Triple H went on to align himself with Shawn Michaels and created DX two years later as his saving grace.

2 Best: Triple H Vs Shawn Michaels (SummerSlam 2002)

SummerSlam 2002 saw the in-ring return of Shawn Michaels. It was the Heartbreak Kid's first match in four years after suffering a career-threatening back injury in a Casket Match at the Royal Rumble in 1998. Triple H turned heel for the first time since May 2001 after teasing a reformation of DX only to blindside Michaels.

RELATED: 10 Times Shawn Michaels Made Legitimate WWE Stars

The two contested an Unsanctioned Street Fight. It was a show-stealing match. HBK was well and truly back by scoring a jackknife cover victory over The Game in his first outing since WrestleMania 14. The Game had the last laugh by attacking Michaels with a Sledgehammer twice in the back. The vicious assault forced Michaels to exit the arena on a stretcher.

1 Worst: Triple H Vs The Great Khali (SummerSlam 2008)

Triple H had the privilege of being WWE Champion at SummerSlam in 2008. It was the first time he had entered SummerSlam as WWE Champion. He had the unfortunate task of defending his title against The Great Khali. Khali, a former World Champion in his own right, had poor in-ring skills. The crowd chanted "You can't wrestle" at Khali.

It was a slow match as expected, which somehow managed to last 10 minutes. Triple H put the crowd out of their misery by delivering a botched Pedigree. It felt like a wasted Championship match at SummerSlam.

NEXT: The 10 Most Heelish Acts Triple H Committed As A Face