Triple H and Shawn Michaels have a long, storied history at SummerSlam —collectively competing in a dozen matches at the annual event. When D-Generation X takes on the McMahons on Aug. 20, The Game and HBK will have a distinct experience advantage, but that doesn’t mean the Chairman and his son Shane should be overlooked by any means. Shane has proven he’s capable of holding his own in the ring — he’s held the Hardcore and European Championships — and former WWE Champion Mr. McMahon has been in brutal battles with Superstars like Stone Cold Steve Austin, Hulk Hogan, and Undertaker.

As for DX, their SummerSlam legacy began in 1989 when Shawn Michaels made his first SummerSlam appearance as one-half of the Rockers. Michaels and his tag team partner, Marty Jannetty, teamed with Tito Santana in a losing effort against Rick Martel and the Rougeau Brothes.

The following year, the Rockers were again on the losing side when Power & Glory (Hercules & Paul Roma) were able to get the pinfall over Jannetty. Prior to the match, Michaels was attacked with a chain by Hercules, but competed in the match even after the assault.

Michaels evolved into the narcissistic Heart Break Kid after throwing Jannetty through a window in January of 1992. He tested his talents in singles competition at SummerSlam for the first time that year, but both he and opponent Rick Martel were counted out.

SummerSlam 1993 saw Michaels break out as a solo star. After winning the Intercontinental Championship late in 1992, he defeated Mr. Perfect to retain the gold. HBK didn’t win on his own, though. His ringside comrade, Diesel, interfered on Michaels’ behalf and rammed Mr. Perfect into the ringpost. Due to the impact, Mr. Perfect was unable to re-enter the ring.  

In 1994, Diesel and Michaels’ roles were reversed. When Diesel took on Razor Ramon for the Intercontinental Championship, partner Michaels was in his corner. Although HBK didn’t compete in the ring, he did affect the outcome when he accidentally gave Diesel Sweet Chin Music, which cost him the match.

The first time Triple H and Shawn Michaels were at SummerSlam together (not as a tag team) was in 1995. That night, both Superstars emerged victorious. In one of the most memorable SummerSlam matches in history, high-flying HBK was victorious in a Ladder Match over Razor Ramon. Michaels retained the Intercontinental gold after climbing the ladder and grabbing the championship.  That same night, Triple H defeated Hardcore Holly after a Pedigree.

Moving from the Intercontinental Championship to the WWE Championship in 1996, The Showstopper scored a pinfall over Vader to retain the coveted WWE Championship. After Vader had won by both count-out and disqualification, manager, Jim Cornette, argued to then-WWE President Gorilla Monsoon that the match should continue; Michaels agreed to keep the contest going, and eventually got the win. 

In 1997, Michaels didn’t compete, but was still involved as the special guest referee in the WWE Championship match between Bret Hart and then-WWE Champion Undertaker. When Michaels accidentally slammed Undertaker with a chair, it gave Hart the opening he needed to capitalize and win his fifth WWE Championship. Triple H did compete but was on the losing end, as he was defeated by Mankind in a Steel Cage Match. After delivering an elbow off of the top of the cage, Mankind was able to escape for the victory. 

While Michaels went into retirement early in 1998, Triple H was building more momentum. As the new leader of DX, he won the Intercontinental Championship from The Rock in a thrilling Ladder Match at SummerSlam 1998. Chyna gave “The People’s Champion” a low blow as he climbed the ladder, allowing The Game to reach the championship first.

The Game competed in a Triple Threat Match against Mankind and Stone Cold for the WWE Championship at SummerSlam in1999. Triple H didn’t win the match, but demonstrated how much winning the championship means to him. He smashed Stone Cold with a steel chair, but was ultimately pinned after Mankind hit a Double-Arm DDT.

The following year, Triple H again competed in another Triple Threat Match for the WWE Championship, but once again came up short. The Rock, the champion at the time, covered The Game to win the bout after Kurt Angle had smashed him in the head with a sledgehammer.

2001 was the first time since 1992 that neither Triple H nor Shawn Michaels didn’t compete at SummerSlam. The next year, however, they made up for it. 2002 marked the first time since 1995 that both men had competed in the same year...and ironically enough, this time they were against each other.

That year, HBK and The Game went head to head in an Unsanctioned Match (a match devoid of WWE guidelines or rules). The bout was a bloody one, and in the end, Michaels was able to reverse The Game’s Pedigree attempt into an inside cradle for the victory. Afterwards, Triple H showed his severe distaste for losing by grabbing his sledgehammer and smashing HBK in the back…twice. The assault was vicious enough for Michaels to need a stretcher to be taken out of the arena.

One year later, both men were once again in the same match. In the second-ever Elimination Chamber Match, HBK, WWE Champion Triple H, Chris Jericho, Kevin Nash, Randy Orton and Bill Goldberg all battled it out for the gold in 2003. When it seemed like nobody could stop Goldberg — he eliminated Orton, Jericho and Michaels — Triple H stepped in with his sledgehammer and took him out for the victory.

Michaels was injured in 2004, but Triple H was at SummerSlam to face Eugene. William Regal came to ringside and used brass knuckles on Ric Flair, which distracted Eugene. The Game took advantage of the situation by hitting Eugene with The Pedigree to get the pinfall.

While Triple H was out the next year, arguably the biggest match in SummerSlam history took place in 2005 between the Icon Hulk Hogan and the Legend Shawn Michaels. HBK seemed to have the victory in hand after he landed Sweet Chin Music on the Hulkster…but it wasn’t enough. Hogan kicked out of the pinfall and used the fans’ cheers to rally a comeback. After landing a Big Boot and a Leg Drop, he covered Michaels for the victory. After the match Michaels showed his respect for Hogan, shaking hands and congratulating him on his victory.

The McMahons are less experienced; in fact, 2006 will mark Mr. McMahon's first time competing at SummerSlam. Now although the Chairman has been present at numerous SummerSlams, he has usually been at ringside or behind the announcers’ table. The Chairman has seen some classic WWE matches in his time, which have no doubt taught him specific maneuvers that can cripple opponents. If there’s one thing to keep in mind about the McMahons, it’s that they should never be counted out under any circumstances. WWE didn’t become the most dominant brand in sports-entertainment because the Chairman rolled over in the face of adversity. He’s a warrior, and will put his life on the line for his company.

His son Shane has competed three times at SummerSlam, compiling a 1-2 record. He faced the 285-pound, rock-solid Test in a "Love Her or Leave Her" at SummerSlam 1999 and martial arts expert Steve Blackman in a Hardcore Match in 2000, but came up short in both contests. After a two-year hiatus, Shane returned in 2003 to defeat Eric Bischoff in a No Disqualification, Falls Count Anywhere Match. Shane has proven that he’s tough, and that he’ll gladly drop the suit for in-ring attire to defend his family’s honor and business.

Experience aside, this rivalry has turned into bitter hatred on both sides. Mr. McMahon is willing to do whatever it takes to destroy the duo that has embarrassed him and his family numerous times over the past few months. Will his disgust for Triple H and Shawn Michaels be enough to propel him and his son to victory? Or, when the referee raises the winners’ hands, will DX have only two words and a crotch-chop for the McMahons?