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1999 - Monday Night Raw
Triple H captured his first World Title when he defeated Mankind on the Monday Night Raw after SummerSlam on August 23, 1999.
1999 - Unforgiven
The Game's next title reign would commence at Unforgiven in 1999. He was able to defeat British Bulldog, The Rock, Kane, Mankind, and Big Show in a Six-Pack Challenge (but not without a courtesy Stunner from guest referee Stone Cold Steve Austin).
January 3, 2000 - Monday Night Raw.
By this time, Triple H was used to being in the main event scene. So when Big Show dethroned him at the 1999 Survivor Series, he took it personally. This was evident when Triple H took back his championship less than two months later on the January 3, 2000 episode of Monday Night Raw. Maybe Show enjoyed this punch a little too much while thinking about the good old days when HHH wasn't his boss...
At Judgement Day on May 21, 2000, Triple H and The Rock added a historic moment to their feud when The Game defeated The Great One in a 60 minute Iron Man match to begin his fourth championship reign.
The Game faced a terrible setback in his career, when in the span of a few days in 2001 he lost the Intercontinental Championship to Kane, lost the Tag Team Championships, and faced a devastating quad tear which kept him out of action for 8 months. Upon his return he won the 2002 Royal Rumble and then defeated Chris Jericho at WrestleMania 18 to become the Undisputed Champion.
When Raw General Manager Eric Bischoff brought the World Heavyweight Championship to Raw, he needed a champion. Triple H's mere presence meant that he should look no further than The Game himself. Bischoff then simples awarded the title to HHH, though he did have to defend against Ric Flair later in the night.
Triple H would find a bitter enemy in his best friend Shawn Michaels, as was evident in their 3 Stages of Hell match at Armageddon in 2002. Triple H won the first fall (a Street Fight) while Michaels won the second (a Steel Cage match). This meant it all came down to a Ladder Match, where The Game shoved HBK through a mountain of tables to claim his 7th World Championship reign.
Then champion Goldberg had been demolishing all comers until he had to deal with Triple H and Kane. HHH would sneak away from this match with his 8th reign as World Champion.
When Randy Orton became World Champion, Triple H didn't hesitate to, in his words, show "the student who was still the master." Orton was quickly kicked out of Evolution and defeated by the Cerebral Assassin at Unforgiven in 2004.
HHH would once again defeat his former protege Randy Orton when he pinned him last during the Elimination Chamber match at New Year's Revolution in 2007 to win his 10th World Title. Little did he know he had another protege to worry about in Batista, who would dethrone The Game at WrestleMania just a few months later.
In one of the craziest nights in perhaps all of WWE history, Randy Orton was awarded the WWE Championship by Mr. McMahon at No Mercy in 2007. Triple H protested and then defeated Orton for the title, only to also defend it against Umaga later in the same night. After this victory, he then defended against Orton, only to lose this time. As the Viper giveth, so he taketh away.
In a Fatal 4-Way Match at Backlash in 2008, Triple H was able to outlast JBL, John Cena, and Randy Orton to win his 12th World Title. With the No Mercy bedlam still on his mind, Triple H didn't intend on leaving without the championship around his waist.
Triple H was able to writhe away Edge's WWE Championship at No Way Out in 2009 when he outlasted Vladimir Kozlov, Jeff Hardy, Big Show, Undertaker, and the Rated-R Superstar himself in an Elimination Chamber match. At the time, this let Triple H set a record for the most WWE Championships held by a single superstar.
Finally, Triple H was able to achieve his 14th Championship reign when he last eliminated Dean Ambrose in the 2016 Royal Rumble to take away Roman Reigns' WWE World Heavyweight Championship.
From the very beginning of his first championship reign to the end of his last, The Game has always been one of the top superstars in the business and will forever be cemented in history as one of the greatest world champions of all time.
