Arguably, one of the greatest superstars of his generation is Triple H. The Cerebral Assassin has 14 World Title reigns to his name, along with five Intercontinental Championships amongst other important accolades.
However, Triple H thrives in being the main event World Title picture, where he has made a name for himself. The Game is unquestionably an iconic figure, and one of the best in the business. There is no doubt that he has earned his position as one of the greatest in the business. Unfortunately, Triple H has a reputation for going into business for himself, and he has often found himself headlining pay-per-views when he shouldn't have.
10 WrestleMania 21 (Vs. Batista)
At WrestleMania 21, Triple H defended the World Heavyweight Championship against Batista. The Animal won the 2005 Royal Rumble match, and he turned his back on his former Evolution mentor with the duo closing out WrestleMania 21.
Ultimately, Batista proved to be too strong for Triple H by clinching his first World Heavyweight Title. However, JBL and John Cena's WWE Championship match should have main evented the show as Layfield's 280-day reign as WWE Champion coming to end to Cena in the main event, would have been a bigger deal.
9 The Great American Bash 2008 (Vs. Edge)
Triple H's run as the face of SmackDown in 2008 was refreshing, which saw him feud with the likes of Jeff Hardy and Edge. The Game successfully retained the WWE Championship against Edge in the main event of The Great American Bash.
It was a sublime match from both men but CM Punk was defending the World Heavyweight Championship on pay-per-view for the first time which was a significant moment in his career. Punk wasn't booked strongly as a World Champion during his first run as champion, and not headlining the show against Batista, didn't help his cause either.
8 Super ShowDown 2018 (Vs. The Undertaker)
Triple H and The Undertaker battled for two decades, and their final singles match emanated from the Melbourne Cricket Ground in Melbourne, Australia at Super ShowDown 2018. Neither came down the aisle alone as Shawn Michaels was in Triple H's corner and Kane gave Undertaker moral support.
Unfortunately, their No Disqualification match went on longer than it needed to with the match lasting 27 minutes. The Game earned a monumental victory over Undertaker, but AJ Styles and Samoa Joe's WWE Championship match certainly was the right choice to close out the show.
7 SummerSlam 2003 (Elimination Chamber Match)
Goldberg was a man on a mission, and he could smell blood in the Elimination Chamber match for Triple H's World Heavyweight Championship at SummerSlam 2003. However, the reigning champ was not functioning at 100% as he was nursing a groin injury, which is why he sported a pair of biker trunks.
This should have been Goldberg's night to win the World Heavyweight Title as he was dominant, but The Game managed to retain the gold. Since Goldberg did not win the championship, Kurt Angle and Brock Lesnar's enthralling WWE Title match was a better option to main event SummerSlam.
6 Survivor Series 2003 (Vs. Goldberg)
Goldberg ended Triple H's remarkable 280-day reign as World Heavyweight Champion at Unforgiven 2003, which led to a rematch between the bitter rivals at Survivor Series 2003. For some reason, Goldberg and The Game did not have chemistry, which is why their matches never clicked.
Nevertheless, despite interference from Evolution, Goldberg retained the World Heavyweight Title. Since it was Survivor Series, the best match of the night was unquestionably the five-on-five elimination match between Team Bischoff and Team Austin. Team Bischoff prevailed which meant Austin was no longer co-Raw GM. That bout should have been the main event.
5 Survivor Series 2017 (Vs. Team SmackDown)
Again, nostalgia reigned supreme in the Survivor Series traditional elimination match that pitted Team Raw and Team SmackDown against each other at the 2017 iteration of the event. Kurt Angle's job as Raw General Manager was on the line, which was a caveat in this contest.
The match wasn't bad, but the decisions were questionable with Shane McMahon going deep and Triple H picking up the win by pinning Shane. Universal Champion Brock Lesnar and WWE Champion AJ Styles' match in the semi-main event position was the perfect match to end Survivor Series.
4 Hell In A Cell 2009 (Vs. Legacy)
DX and Legacy's feud dominated large portions of 2009, which saw Triple H and Shawn Michaels collide with Ted DiBiase and Cody Rhodes at Hell in a Cell. They clashed in a tag team Hell in a Cell match which surprisingly main evented the show. Both teams boasted a victory over each other on pay-per-view, so this was the decider.
Legacy removed Triple H from the equation early on, which led Michaels to fend for himself. Nonetheless, The Game returned and DX prevailed in a match they didn't need to win. John Cena and Randy Orton's marquee WWE Championship match was the viable option to main event the show but it failed to do so.
3 WrestleMania 25 (Vs. Randy Orton)
Traditionally, World Championship matches close out WrestleMania, which seems to be the logical decision. Triple H's WWE Title match against Randy Orton managed to headline WrestleMania 25, but they suffered drastically as Undertaker and Shawn Michaels tore the house down in a five-star instant classic.
Fans were burned out from Undertaker and Michaels' epic, which is why their main event fell flat. The Game and Orton battled frequently, whereas a match of the caliber between Undertaker and Michaels rarely happened, with both being on different shows. Undertaker and Michaels closing out the show made sense, and with The Game retaining, it put a dampener on WrestleMania.
2 WrestleMania X8 (Vs. Chris Jericho)
Triple H hoped to cap off a strong start to 2002 by defeating Chris Jericho for the Undisputed WWE Championship at WrestleMania X8. Jericho and Triple H knew that they were dealt a tough hand, as Hulk Hogan and The Rock put on a memorable match that captivated the audience.
In fairness to Jericho and Triple H, they were unfortunate that their match was overshadowed, as they put on a decent match which fans sadly weren't interested in. Triple H reclaimed his throne, which seemed underwhelming. Hogan's first 'Mania outing in nine years was a huge deal, and it deserved to close out the show, with Rock prevailing in a blockbuster match that lived up to the billing.
1 Vengeance 2006 (Vs. The Spirit Squad)
Triple H and Shawn Michaels reformed DX in 2006, but the veterans' first feud was with Mr. McMahon's lapdogs, The Spirit Squad. The Spirit Squad were not in DX's league, and they were hung out to dry in their rivalry, which saw DX get the upper hand.
The main event at Vengeance 2006 featured DX overcoming Spirit Squad in a 5-0n-2 handicap match. That was expected, but Rob Van Dam's WWE Championship title match with Edge was the match of the night, and with it being RVD's first title defense on pay-per-view, he deserved to have the spotlight on him in the main event.