Triple H vs. Mr. McMahon in a Street Fight

On the November 29, 1999 edition of Raw, Stephanie McMahon was to marry Test. Mr. McMahon warned Triple H and DX to stay clear of the ceremony. However, moments before her nuptials, Triple H shocked the Chairman and the world as he revealed he had married the “Billion Dollar Princess” himself when she was drugged in Las Vegas. The Chairman was irate because the McMahon family name had been dishonored; therefore he challenged Triple H to a match at Armageddon.

The match would be a Street Fight with the following stipulations: if Mr. McMahon defeated Triple H, the marriage between Stephanie and The Game would be annulled. If Triple H defeated his father-in-law, he would receive another opportunity at the WWE Championship. The Street Fight between the two men was a brutal affair, which included an emotional Stephanie seated at ringside, watching as her father battled the man she was tricked into marrying. Triple H underestimated the Chairman, as Mr. McMahon unleashed an offensive arsenal, looking to cripple The Game.

After the bloodbath went back and forth, and Mr. McMahon looked to finish off Triple H with a sledgehammer, young Stephanie entered the ring and begged her father to let her finish the job. Stephanie could not muster the courage to destroy Triple H, and instead The Cerebral Assassin grabbed the sledgehammer and smashed his opponent. The Game then pinned the Chairman and turned his sights on Stephanie. The two stared each other down, and Triple H and Stephanie revealed to the world their plans as they embraced each other in the center of the ring and the McMahon-Helmsley era was born. Over the next ten months, they would rule WWE, making their own rules and raising hell for the rest of the Superstars of Raw and SmackDown.

On this night, Mr. McMahon brought Triple H to the brink for the honor of his family, but in the end Stephanie McMahon cemented her place as one of the most hated performers in WWE history as she turned her back on her father.